77448-58-9

Usage

Uses

Used in Pharmaceutical Industry:
(2S)-amino(1-hydroxycyclopropyl)ethanoic acid is used as a chiral building block for the synthesis of pharmaceutical compounds, leveraging its unique structural features and potential reactivity to create novel drugs with enhanced efficacy and selectivity.
Used in Biochemical Research:
(2S)-amino(1-hydroxycyclopropyl)ethanoic acid serves as a valuable research tool in biochemistry, enabling scientists to study its interactions with biological systems and explore its potential as a modulator of specific biochemical pathways or processes. Further research is necessary to fully understand its properties and applications.

Upstream product

• 377090-73-8 (R)-benzyl 4-(1-hydroxycyclopropyl)-2,2-dimethyloxazolidine-3-carboxylate 
• 377090-74-9 1-(1-(benzyloxycarbonylamino)-2-hydroxyethyl)-1-hydroxycyclopropane 
• 377090-75-0 (S)-N-carbobenzyloxycleonin 
• 139132-15-3 benzyl 2-<1-(benzyloxy)cyclopropyl>-2-chloroacetate 
• 82979-45-1 methyl 2-chloro-2-cyclopropylideneacetate 
• 139132-49-3 benzyl 2-azido-2-<1-(benzyloxy)cyclopropyl>acetate 
• 77369-33-6 Amino-[1-(1-ethoxy-ethoxy)-cyclopropyl]-acetic acid 
• 77369-32-5 Amino-[1-(1-ethoxy-ethoxy)-cyclopropyl]-acetonitrile 

Relevant academic research and scientific papers

First stereocontrolled synthesis of (S)-cleonin and related cyclopropyl-substituted amino acids.

[reaction: see text]. Enantiomerically pure (S)-cleonin, a key component of the antitumor antibiotic cleomycin, was prepared starting from (R)-serine. The Kulinkovich cyclopropanation of the methyl ester of N-Cbz serine acetonide gave the hydroxycyclopropyl moiety. The amino alcohol region was further oxidized to amino acid. The Kulinkovich cyclopropanation allowed also the preparation of other non-natural substituted cyclopropylglycines.

A New Versatile Synthesis of Ring-Substituted 2-Cyclopropylglycines and Related Amino Acids

Alkyl 2-chloro-2-cyclopropylideneacetates 2 serve as universal starting materials for a new general synthesis of cyclopropylglycines by a simple three- to four-step methodology. 1,4-Addition of nucleophiles, substitution with azide ion, and mild catalytic

SYNTHESIS OF CLEONINE, AMINO(1-HYDROXYCYCLOPROPYL)ACETIC ACID, A NOVEL AMINO ACID CONTAINED IN CLEOMYCIN

The synthesis of cleonine, amino(1-hydroxycyclopropyl)acetic acid, a novel amino acid contained in cleomycin, a new bleomycin-phleomycin group antibiotic, is described.