692778-41-9

Usage

Uses

Used in Organic Synthesis:
(+)-(S,S)-2-benzyloxymethylenecyclopropane-1-carboxylic acid ethyl ester is used as a building block in organic synthesis for the creation of complex organic molecules. Its unique structure allows it to undergo various chemical reactions, facilitating the synthesis of a wide range of compounds.
Used in Pharmaceutical Research:
In the pharmaceutical industry, (+)-(S,S)-2-benzyloxymethylenecyclopropane-1-carboxylic acid ethyl ester is used as a key intermediate in the development of new drugs and pharmaceuticals. Its potential applications in medicinal chemistry make it a promising candidate for the synthesis of novel therapeutic agents.
Overall, (+)-(S,S)-2-benzyloxymethylenecyclopropane-1-carboxylic acid ethyl ester is a versatile compound with interesting chemical properties and potential uses in pharmaceutical research and development, as well as in the broader field of organic synthesis.

Upstream product

• 867-13-0 diethoxyphosphoryl-acetic acid ethyl ester 
• 2930-05-4 (S)-benzyl glycidyl ether 

Downstream Products

• 692778-42-0 ((1S,2S)-2-Benzyloxymethyl-cyclopropyl)-carbamic acid tert-butyl ester 
• 1932779-15-1 (1S,2S)-2-Benzyloxymethyl-cyclopropanecarboxylic acid 

Relevant academic research and scientific papers

Synthesis of Enantiomerically Pure 1,2,3-Trisubstituted Cyclopropane Nucleosides Using Pd-Catalyzed Substitution via Directing Group-Mediated C(sp3)-H Activation as a Key Step

A series of enantiomerically pure 1,2,3-trisubstituted cyclopropane nucleosides Ia-Id and IIa-IId of medicinal chemical interest was designed and synthesized. In the synthesis, a Pd-catalyzed substitution reaction via a directing group-mediated C(sp3

A convenient chemo-enzymatic synthesis and 18F-labelling of both enantiomers of trans-1-toluenesulfonyloxymethyl-2-fluoromethyl-cyclopropane

The present report is concerned with a stereoselective, reliable route to trans-1,2-disubstituted cyclopropanes and in particular to (S,S)-1- tosyloxymethyl-2-fluoromethyl-cyclopropane (1) and (R,R)-1-tosyloxymethyl-2- fluoromethyl-cyclopropane (ent-1) as conformationally restricted, terminally fluorinated C4-building blocks for medicinal chemistry. The enzymatic kinetic resolution based synthesis of 1 and ent-1 utilises inexpensive, commercially available starting materials. It is based on enantiomeric resolution of rac-cyclopropane carboxylic esters using esterase from Streptomyces diastatochromogenes. Both enantiomers of 1 were prepared selectively in high overall yield over nine steps, starting from ethyl acrylate. The successful radiosynthesis of [18F]-1 and [18F]-ent-1 is also reported.

Total synthesis of (+)-belactosin A.

A concise first total synthesis of the antitumour antibiotic belactosin A is reported, involving coupling of beta-lactone carboxylic acid 3 with N-Ala-aminocyclopropyl alanine 11.

Stereocontrolled synthesis of 3-(trans-2-aminocyclopropyl)alanine, a key component of belactosin A

(Matrix presented) Herein we report a concise synthesis of 3-(trans-2-aminocyclopropyl)alanine, a component of belactosin A, using asymmetric alkylation of a glycine enolate in the presence of chiral phase-transfer catalysts to control the configuration at C2. Reaction of protected glycidol with triethyl phosphonoacetate (Wadsworth-Emmons cyclopropanation) is used for enantiospecific preparation of an intermediate cyclopropanecarboxylate that is converted to a cyclopropylamine via Curtius rearrangement.