4-[[(1,1-Dimethylethoxy)carbonyl]amino]-2-cyclopentene-1-carboxylic acid methyl ester, CAS No. 168683-02-1

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168683-02-1

Catalog No. EBD24252

CAS 168683-02-1

Name 4-[[(1,1-Dimethylethoxy)carbonyl]amino]-2-cyclopentene-1-carboxylic acid methyl ester

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Basic Information

Synonyms: (1s,4r)-methyl4-((tert-butoxycarbonyl)amino)cyclopent-2-enecarboxylate methyl4-((tert-butoxycarbonyl)amino)cyclopent-2-enecarboxylate peramivirintermediate cis-(1s,4r)-4-boc-amino-2-cyclopentene-1-carboxylicacidmethylester 4-[[(1,1-Dimethylethoxy)Carbonyl]Amino]-2-Cyclopentene-1-CarboxylicAcidMethylEster 2-cyclopentene-1-carboxylicacid,4-[[(1,1-dimethylethoxy)carbonyl]amino]-,methylester,(1S,4R)- Methyl(1S,4R)-4-[(tert-butoxycarbonyl)amino]cyclopent-2-ene-1-carboxylate (1S,4R)-methyl 4-(tert-butoxycarbonyl)cyclopent-2-enecarboxylate (1S,4R)-methyl-4-(tert-butoxycarbonyl)cyclopent-2-enecarboxylate

Molecular Formula: C12H19NO4

Molecular Weight: 241.28

Categories: Medicinal Chemistry > Pharmaceutical Intermediates > Chiral Intermediates Medicinal Chemistry > Biochemicals and Life Science Reagents > Peptides and Peptidomimetics

Product Description:

(1S,4R)-Methyl 4-((tert-butoxycarbonyl)amino)cyclopent-2-enecarboxylate is a chiral, bicyclic amino acid derivative. Its structure features a cyclopentene ring substituted with a methyl ester group and a tert-butoxycarbonyl (Boc)-protected amino group, with defined (1S,4R) stereochemistry. This compound serves as a crucial, conformationally constrained building block in medicinal chemistry. Its primary application is as a key intermediate in the synthesis of complex bioactive molecules, particularly peptidomimetics and protease inhibitors. The rigid cyclopentene scaffold is used to mimic peptide turn structures or to restrict the conformational freedom of peptide chains, thereby enhancing metabolic stability, potency, and selectivity. It has been employed in research targeting various diseases, including viral infections (e.g., HCV protease inhibitors) and other conditions where modulation of protein-protein interactions is desired. As a Boc-protected, enantiomerically pure intermediate, it is valuable for solid-phase and solution-phase peptide synthesis. Its defined stereochemistry is essential for achieving the desired biological activity in the final drug candidates. This compound is typically used in research and development settings rather than in bulk manufacturing.

Physical Properties

Storage: −20°C