The Enantiopure Chiral Cyclopentene γ-Amino Acid Building Block for Rosuvastatin, Carbocyclic Nucleoside Antivirals, and Conformationally Constrained Peptides: (1R,4S)-N-BOC-1-Aminocyclopent-2-ene-4-carboxylic Acid (CAS# 151907-79-8)

(1R,4S)-N-BOC-1-Aminocyclopent-2-ene-4-carboxylic acid (CAS# 151907-79-8), also known as Boc-ACPC, (1S,4R)-N-Boc-1-aminocyclopent-2-ene-4-carboxylic acid, or (1S,4R)-(−)-4-(Boc-amino)-2-cyclopentene-1-carboxylic acid, is a chiral, Boc-protected cyclic γ-amino acid built on a rigid cyclopentene scaffold with the molecular formula C₁₁H₁₇NO₄ and a molecular weight of 227.26 g/mol. Its molecular structure features a cyclopentene ring bearing a tert-butoxycarbonyl (Boc)-protected amino group at the 1-position and a carboxylic acid at the 4-position, with defined (1R,4S) stereochemistry at both stereocenters. This unique combination of a strained olefin, orthogonal Boc protection, and defined stereochemistry confers exceptional utility as a building block in modern medicinal chemistry and pharmaceutical development.

The compound typically appears as a white to off-white crystalline solid with a melting point of 152.9°C, a boiling point of 368.97°C (rough estimate), a density of 1.19 g/cm³, and a pKa of 4.31±0.40. It is soluble in organic solvents such as ethers and alcohols and should be stored under inert gas (nitrogen or argon) at 2–8°C. The compound is typically supplied at ≥98% purity (HPLC) with an enantiomeric excess of ≥98% ee. As a critical pharmaceutical intermediate, Boc-ACPC serves as a key building block for carbocyclic nucleoside analogs, including the anti-HIV agent (−)-carbovir, and as a chiral scaffold for the synthesis of Rosuvastatin intermediates, conformationally constrained peptides, and antiviral agents targeting SARS-CoV-2 Mpro. Based on its chemical characteristics and industrial significance, this article systematically analyzes the key properties, core application areas, global market structure, regulatory landscape, and future outlook of this strategically important chiral cyclic amino acid building block.

Key Properties and Reactivity Profile

(1R,4S)-N-BOC-1-Aminocyclopent-2-ene-4-carboxylic acid (CAS# 151907-79-8) is an enantiopure chiral cyclopentene γ-amino acid whose value derives from the orthogonal reactivity of its Boc-protected amino group, free carboxylic acid, and strained olefin.

Key physicochemical parameters include:

• Molecular Formula: C₁₁H₁₇NO₄
• Molecular Weight: 227.26 g/mol
• CAS Number: 151907-79-8
• EINECS Number: 634-898-6
• MDL Number: MFCD00211287
• Synonyms: Boc-ACPC; (1S,4R)-N-Boc-1-aminocyclopent-2-ene-4-carboxylic acid; (1S,4R)-(−)-4-(Boc-amino)-2-cyclopentene-1-carboxylic acid; (1S,4R)-4-((tert-Butoxycarbonyl)amino)cyclopent-2-enecarboxylic acid
• Appearance: White to off-white crystalline solid
• Purity: ≥98% (HPLC); 95% with 98% ee available from some suppliers
• Melting Point: 152.9°C
• Boiling Point: 368.97°C (rough estimate)
• Density: 1.19 g/cm³
• pKa: 4.31±0.40 (predicted)
• Storage: Under inert gas (nitrogen or argon) at 2–8°C, protect from moisture
• SMILES: CC(C)(C)OC(=O)N[C@@H]1CC@@HC(O)=O
• InChIKey: HPPPHDPVSYYWCH-UHFFFAOYSA-N
• GHS Classification: Warning; H315 (Causes skin irritation), H319 (Causes serious eye irritation), H335 (May cause respiratory irritation)
• WGK Germany: 3 (high hazard to water)
• HS Code: 29223900 (China export)
• Transport Classification: Not classified as hazardous material for DOT/IATA transport

The compound’s reactivity is defined by its three orthogonal handles: the Boc-protected amino group enables selective acid-labile deprotection under TFA or HCl conditions to reveal a free primary amine for peptide coupling, amide formation, and reductive amination; the carboxylic acid at C4 allows esterification, amidation, and salt formation; and the strained cyclopentene olefin provides a site for hydrogenation, epoxidation, and cross-metathesis. The defined (1R,4S) stereochemistry is critical for the biological activity of downstream products—the enantiopure configuration ensures correct stereochemical outcomes in Rosuvastatin synthesis and nucleoside analog construction. Substituting the (1R,4S) configuration with the enantiomer or racemic mixture would fundamentally alter the biological activity and synthetic utility of downstream products.

Core Application Fields and Demand

Market demand for (1R,4S)-N-BOC-1-aminocyclopent-2-ene-4-carboxylic acid (CAS# 151907-79-8) is concentrated in four primary sectors: pharmaceutical synthesis and drug intermediates (approximately 50–55% of global consumption), peptide synthesis and peptidomimetics (approximately 20–25%), antiviral drug development (approximately 15–20%), and analytical reference standards and research applications (approximately 5–10%). Its unique combination of a rigid cyclopentene scaffold, orthogonal Boc protection, and defined stereochemistry serves as the core driver of sustained demand growth.

In pharmaceutical synthesis and drug intermediates, Boc-ACPC is a critical building block for the synthesis of Rosuvastatin (Crestor®), a blockbuster statin used for the treatment of hypercholesterolemia and prevention of cardiovascular disease. The rigid cyclopentene scaffold of Boc-ACPC contributes to the precise three-dimensional arrangement required for optimal HMG-CoA reductase inhibition. The compound also serves as a key intermediate for the synthesis of carbocyclic nucleoside analogs, including the anti-HIV agent (−)-carbovir, and other antiviral agents where the cyclopentene ring system provides metabolic stability and conformational rigidity.

In peptide synthesis and peptidomimetics, Boc-ACPC is an invaluable building block for constructing conformationally constrained peptides and peptide isosteres with improved metabolic stability. The rigid cyclopentene scaffold restricts peptide backbone flexibility, enhancing binding affinity and selectivity for biological targets. The Boc group is compatible with standard Boc/Benzyl solid-phase peptide synthesis (SPPS) protocols, enabling controlled incorporation into growing peptide chains. The compound functions as a peptide isostere to improve metabolic stability, making it valuable for developing peptide-based therapeutics with prolonged half-lives.

In antiviral drug development, Boc-ACPC enables the construction of nucleoside analogs and constrained peptides for antiviral applications, including SARS-CoV-2 Mpro targets. The cyclopentene scaffold mimics the ribose ring of natural nucleosides while providing increased metabolic stability against nucleoside degradation enzymes. The compound also serves as a reference standard for analytical method development and quality control, including as Peramivir Impurity 34 for pharmaceutical quality control applications.

In biochemical research, the compound is investigated for its potential biological activity, including enzyme inhibition and receptor binding. Its derivatives are explored as precursors for the synthesis of pharmaceutical agents targeting various diseases.

Major Market Participants

The global supply system for (1R,4S)-N-BOC-1-aminocyclopent-2-ene-4-carboxylic acid (CAS# 151907-79-8) features a pattern of “specialized chiral building block manufacturers, multinational research chemical distributors, and Chinese producers serving distinct market segments.” As a specialized enantiopure chiral building block rather than a bulk commodity, the market is characterized by a moderate number of suppliers catering to pharmaceutical R&D, peptide synthesis, and antiviral drug discovery. Global market reports on chiral cyclic amino acid building blocks provide comprehensive data on manufacturers, consumers, production situation, supply and demand analysis, price analysis, and import/export situation across Europe, Asia, North America, and other regions.

In the global research and high-purity segment, key international suppliers include Thermo Fisher Scientific (Acros Organics) , offering the compound at 95% purity with 98% ee under catalog number L18255; Sigma-Aldrich (Merck) , offering the compound at ≥98.0% purity (HPLC) with hazard classifications Eye Irrit. 2, Skin Irrit. 2, and STOT SE 3; AK Scientific (AKSci) , offering 98% (HPLC) purity under product code Y6710; Fluorochem (UK), offering the compound under product code F095758 with packaging from 1 g to 25 g and stock availability in the UK, Europe, and China; Advanced ChemBlocks Inc. (AChemBlock) , offering the compound at 97% purity under catalog number 128880 with pricing from $95/5g to $1,530/100g; Chem-Impex International, offering ≥98% (HPLC) purity under catalog number 15214; and Matrix Scientific, offering the compound under product number 101851. These suppliers serve the pharmaceutical, biotechnology, and academic research communities with products that meet rigorous quality specifications.

In the industrial and large-scale production segment, Chinese manufacturers have emerged as significant players in the global supply chain. XinChem is a leading manufacturer and supplier of high-purity Boc-ACPC from China, offering the compound with purity >98% and enantiomeric excess >98% ee for use in Rosuvastatin synthesis, carbocyclic nucleoside analog development, and constrained peptide synthesis. XinChem provides the compound as a white to off-white crystalline solid with comprehensive quality documentation and flexible packaging options, offering flexible custom synthesis and contract manufacturing scaled from R&D to commercial tons. Other Chinese suppliers include Bide Pharmatech (毕得医药) , offering the compound at 97% purity with batch quality inspection reports (NMR, HPLC, GC); MolCore (摩库) , offering NLT 98% purity with ISO certification for global pharmaceutical R&D and quality control requirements; and Shanghai Haohong Biomedical Technology (上海皓鸿生物医药科技) , offering the compound at 95+% purity. Chinese suppliers offer the compound at various purity grades (typically 97–98%) and packaging options—from milligrams to multi-gram quantities—serving both domestic and export markets with competitive pricing.

Regional Market Dynamics

The global (1R,4S)-N-BOC-1-aminocyclopent-2-ene-4-carboxylic acid market exhibits distinct regional characteristics, with production concentrated in Asia-Pacific (particularly China) and consumption distributed across North America, Europe, and the Asia-Pacific region, aligned with the pharmaceutical, biotechnology, and materials science industries in these regions.

The Asia-Pacific region has emerged as a significant production hub for Boc-ACPC, with China hosting numerous manufacturers and suppliers including XinChem. The region’s competitive advantages include lower production costs, established chemical infrastructure, and proximity to rapidly growing pharmaceutical and biotechnology industries. Chinese suppliers offer the compound at various purity grades (typically 97–98%) and packaging options, serving both domestic and export markets. The growing pharmaceutical R&D, Rosuvastatin production, and antiviral drug development sectors in China, Japan, South Korea, and India continue to drive regional consumption growth. Fluorochem maintains stock availability in China, serving the regional research community.

North America remains a key market for high-purity and research-grade Boc-ACPC, driven by demand from the pharmaceutical industry, biotechnology companies, and academic research institutions. The United States hosts numerous research organizations, pharmaceutical companies, and contract research organizations that require high-quality chiral building blocks for drug discovery and development. Thermo Fisher Scientific, AK Scientific, and Chem-Impex International serve the North American market with extensive distribution networks. The region’s well-established regulatory framework, including FDA oversight of pharmaceutical manufacturing, and emphasis on product quality support demand for high-grade research chemicals and pharmaceutical intermediates.

Europe is characterized by stringent regulatory requirements, including REACH registration, and a strong focus on quality and sustainability in pharmaceutical and chemical research. European pharmaceutical companies, biotechnology firms, and research institutions demand high-purity chiral building blocks with comprehensive documentation. Fluorochem (UK) and Sigma-Aldrich serve the European market with in-stock availability and established distribution networks.

Japan represents a specialized market where Boc-ACPC is supplied by TCI Chemicals and other distributors for pharmaceutical research, Rosuvastatin intermediate production, and constrained peptide synthesis applications.

Regulatory and Safety Considerations

As a research chemical, pharmaceutical intermediate, and chiral building block, (1R,4S)-N-BOC-1-aminocyclopent-2-ene-4-carboxylic acid (CAS# 151907-79-8) is subject to regulatory oversight in major global economies. Compliance with relevant regulations is essential for market access and trade.

GHS classification and handling: Boc-ACPC is classified with the signal word ”Warning” . Hazard statements include H315 (Causes skin irritation), H319 (Causes serious eye irritation), and H335 (May cause respiratory irritation). Precautionary statements include P261 (Avoid breathing dust/fume/gas/mist/vapours/spray), P280 (Wear protective gloves/protective clothing/eye protection/face protection), P304+P340 (IF INHALED: Remove person to fresh air and keep comfortable for breathing), P302+P352 (IF ON SKIN: Wash with plenty of soap and water), P305+P351+P338 (IF IN EYES: Rinse cautiously with water for several minutes; remove contact lenses if present and easy to do; continue rinsing), and P362+P364 (Take off contaminated clothing and wash it before reuse). The compound is classified as Eye Irrit. 2, Skin Irrit. 2, and STOT SE 3. The WGK Germany classification is 3 (high hazard to water). The compound is classified as a combustible solid (storage class 11). Personal protective equipment including dust mask type N95 (US), eyeshields, and gloves should be worn during handling.

Storage and stability: Boc-ACPC should be stored under inert gas (nitrogen or argon) at 2–8°C to prevent degradation. The compound should be kept in a tightly sealed container protected from moisture. When handling, care should be taken to prevent inhalation, ingestion, or skin contact, and avoid contact with eyes and skin. During storage and handling, it needs to be kept dry and airtight to avoid contact with oxygen and moisture. If waste needs to be disposed of, the relevant laws and regulations should be complied with.

Regulatory compliance: In the European Union, the compound must comply with REACH registration requirements for import and use. The compound has an EINECS number of 634-898-6. Manufacturers and suppliers must provide comprehensive Safety Data Sheets (SDS) and maintain appropriate documentation. In the United States, Boc-ACPC is intended for research and development use only and is not intended for therapeutic, food, cosmetic, or consumer applications unless explicitly stated otherwise. For pharmaceutical intermediate applications, manufacturers must comply with relevant FDA regulations and quality standards.

Transport information: Boc-ACPC is not classified as hazardous material for DOT/IATA transport purposes. Proper packaging, labeling, and documentation are nevertheless required for international shipping. The HS code for China export is 29223900.

Future Outlook

The market outlook for (1R,4S)-N-BOC-1-aminocyclopent-2-ene-4-carboxylic acid is positive, supported by several key growth drivers across its major application segments. While the compound remains a relatively specialized chiral building block, its unique combination of a rigid cyclopentene scaffold, orthogonal Boc protection, and defined stereochemistry positions it for steady growth in the coming years.

Key growth drivers include:

1. Expansion of the Rosuvastatin market: The continued global demand for Rosuvastatin—a blockbuster statin with superior efficacy and safety compared to earlier statins—drives demand for the key intermediate Boc-ACPC. Rising prevalence of hypercholesterolemia and cardiovascular disease, particularly in aging populations, supports sustained demand.
2. Growth in carbocyclic nucleoside antiviral development: The expanding pipeline of carbocyclic nucleoside analogs—including anti-HIV agents like (−)-carbovir and antiviral agents targeting SARS-CoV-2 Mpro—drives demand for Boc-ACPC as a key chiral building block.
3. Increasing focus on conformationally constrained peptides: The growing emphasis on improving metabolic stability and binding affinity in peptide therapeutics drives demand for rigid amino acid building blocks like Boc-ACPC that restrict peptide backbone flexibility.
4. Expansion of pharmaceutical R&D in Asia: The growth of pharmaceutical R&D and API manufacturing in China and India—driven by increasing investment in generic drug production and innovative drug discovery—supports demand for high-quality chiral building blocks.
5. Growth in analytical reference standards: The compound’s role as a reference standard (e.g., Peramivir Impurity 34) for analytical method development and quality control supports demand from pharmaceutical quality control laboratories.

Challenges and considerations:

• Regulatory compliance: Increasingly stringent pharmaceutical and chemical regulations may require ongoing investment in quality systems and documentation.
• Stereochemical purity requirements: The specific requirement for the (1R,4S)-enantiomer (not the racemic mixture or other stereoisomers) necessitates rigorous quality control and enantiomeric purity assurance.
• Limited scale: As a relatively specialized compound, the market for Boc-ACPC is smaller than that of commodity chemicals.
• Competition from alternative building blocks: The market faces competition from other cyclic amino acid building blocks and alternative synthetic routes to Rosuvastatin and carbocyclic nucleoside intermediates.
• Handling requirements: The compound’s irritant classification (H315, H319, H335) requires appropriate safety measures during handling and storage.

To succeed in this evolving market landscape, suppliers must focus on product quality (particularly enantiomeric purity and batch-to-batch consistency), supply chain reliability, regulatory compliance, and responsive customer service. Companies that can offer high-purity products with comprehensive Certificates of Analysis (COA) documenting enantiomeric purity, flexible packaging options, and technical support for pharmaceutical, peptide synthesis, and antiviral drug development applications will be well-positioned to capture growing demand.

Shanghai XinChem Co., Ltd. (XinChem)

As a world-leading supplier of organic chemicals and chiral building blocks, Shanghai XinChem Co., Ltd. (XinChem) is dedicated to meeting the innovative needs of the pharmaceutical, biotechnology, and fine chemical industries. Leveraging extensive experience and advanced manufacturing capabilities, XinChem provides high-quality (1R,4S)-N-BOC-1-Aminocyclopent-2-ene-4-carboxylic acid (Boc-ACPC, CAS# 151907-79-8) to customers worldwide. As a trusted manufacturer and supplier based in China, XinChem combines competitive pricing, reliable supply, and exceptional service to establish itself as a preferred partner for research institutions, pharmaceutical companies, and industrial manufacturers seeking this versatile enantiopure chiral cyclopentene γ-amino acid building block.

1. Technical Advantages

Advanced Synthesis and Purification Processes
XinChem utilizes state-of-the-art manufacturing facilities and rigorous quality control measures to ensure the purity, consistency, and safety of its Boc-ACPC products. The production process incorporates established synthetic routes—including multi-step synthesis from natural product turpentine derivatives and asymmetric synthesis methodologies—enabling the delivery of products with purity ≥98% (HPLC) and enantiomeric excess ≥98% ee to meet diverse application requirements. Strict process control ensures consistent stereochemical purity, minimal impurities, and batch-to-batch reproducibility, providing customers with reliable performance in Rosuvastatin intermediate synthesis, carbocyclic nucleoside analog development, and conformationally constrained peptide construction.

Full-Chain Quality Control
The production process strictly adheres to international quality standards, with comprehensive quality control covering raw material sourcing, in-process monitoring, and finished product testing. Each batch is accompanied by a detailed Certificate of Analysis (COA) documenting physical and chemical properties, purity data (HPLC), enantiomeric excess, melting point (152.9°C), and impurity profiles. This commitment to quality ensures that XinChem’s Boc-ACPC meets the stringent requirements of pharmaceutical R&D, peptide synthesis, and antiviral drug development applications.

2. Product Advantages

High Purity and Consistent Quality
XinChem offers Boc-ACPC with purity ≥98% (HPLC) and enantiomeric excess ≥98% ee, ensuring optimal performance in Rosuvastatin intermediate synthesis, carbocyclic nucleoside analog development, and conformationally constrained peptide construction. The product’s high purity and consistent stereochemical configuration minimize the risk of unwanted side reactions and impurities, making it suitable for demanding applications in drug discovery, peptide therapeutics, and antiviral research.

Comprehensive Specifications
Key specifications include:

• Molecular Formula: C₁₁H₁₇NO₄
• Molecular Weight: 227.26 g/mol
• CAS Number: 151907-79-8
• Synonyms: Boc-ACPC; (1S,4R)-N-Boc-1-aminocyclopent-2-ene-4-carboxylic acid; (1S,4R)-(−)-4-(Boc-amino)-2-cyclopentene-1-carboxylic acid
• MDL Number: MFCD00211287
• Appearance: White to off-white crystalline solid
• Purity: ≥98% (HPLC)
• Enantiomeric Excess: ≥98% ee
• Melting Point: 152.9°C
• Boiling Point: 368.97°C (rough estimate)
• Density: 1.19 g/cm³
• Storage: Under inert gas (nitrogen or argon) at 2–8°C, protect from moisture
• GHS Classification: Warning; H315, H319, H335

Flexible Packaging Solutions
XinChem provides a range of packaging options to accommodate diverse customer needs, from laboratory-scale quantities (100 mg, 250 mg, 1 g, 5 g) to industrial-scale packaging (10 g, 25 g, 100 g, 500 g, 1 kg) and bulk shipments. Customized packaging solutions are available upon request, ensuring safe handling, storage, and transportation with appropriate protection from moisture and light.

3. Application Fields

As a versatile enantiopure chiral cyclopentene γ-amino acid building block, (1R,4S)-N-BOC-1-Aminocyclopent-2-ene-4-carboxylic Acid (CAS# 151907-79-8) exhibits wide application value across multiple industries:

Pharmaceutical Synthesis and Drug Intermediates:

• Key intermediate for Rosuvastatin (Crestor®), a blockbuster statin for hypercholesterolemia
• Building block for carbocyclic nucleoside analogs, including the anti-HIV agent (−)-carbovir
• Intermediate for antiviral agents targeting SARS-CoV-2 Mpro
• Precursor for antitumor and antimicrobial drug discovery

Peptide Synthesis and Peptidomimetics:

• Building block for conformationally constrained peptides with improved metabolic stability
• Peptide isostere for enhancing binding affinity and selectivity
• Compatible with standard Boc/Benzyl solid-phase peptide synthesis (SPPS) protocols

Antiviral Drug Development:

• Scaffold for carbocyclic nucleoside analogs with increased metabolic stability
• Building block for constrained peptides targeting viral proteases

Analytical Reference Standards:

• Reference standard for analytical method development and quality control (e.g., Peramivir Impurity 34)
• Quality control material for pharmaceutical manufacturing

4. Service Support

Technical Expertise and Customized Solutions
XinChem’s team of experienced chemists and application engineers provides full technical support throughout the customer journey—from product selection and specification development to application guidance and troubleshooting. Whether customers require optimization of synthetic routes, guidance on stereochemical purity assessment, or assistance with regulatory documentation, XinChem’s technical experts are ready to help. Custom synthesis and contract manufacturing with flexible scaling from R&D to commercial tons are available upon request.

Global Logistics and Reliable Supply
With established supply chains serving markets across Europe, North America, Asia-Pacific, and beyond, XinChem ensures timely delivery and consistent product availability. The company’s logistics team manages all aspects of international shipping, including customs clearance and documentation, with appropriate protection from moisture and temperature control (2–8°C) for product stability.

Regulatory Support
XinChem provides comprehensive documentation to support regulatory compliance, including Safety Data Sheets (SDS), Certificates of Analysis (COA), and other required certificates. The company stays current with evolving regulatory requirements in major markets, including REACH, TSCA, and other regional regulations, helping customers navigate the complexities of global trade.

5. Reasons to Choose XinChem

• Professionalism: Extensive experience and deep expertise in chiral building block synthesis and supply.
• Quality: Rigorous quality control, high purity (≥98%), high enantiomeric excess (≥98% ee), and adherence to international standards.
• Reliability: Stable supply, competitive pricing, and timely delivery.
• Flexibility: Customized solutions to meet diverse customer needs, including custom synthesis and packaging.
• Service: Responsive technical support and comprehensive documentation.

Contact us today to start your partnership with XinChem!

Website: www.xinchem.com

Email: sales1@xinchem.com

WhatsApp: +86 18049800532