1638768-80-5

Usage

Uses

Used in Pharmaceutical Industry:
(1S,2S)-1-[[(N-tert-butoxycarbonyl)amino]methyl]-carboxycyclopropane is used as a versatile building block for the synthesis of complex organic molecules, particularly in the preparation of pharmaceuticals. Its unique stereochemistry and functional groups enable the development of new drugs with specific therapeutic targets.
Used in Agrochemical Industry:
In the agrochemical industry, (1S,2S)-1-[[(N-tert-butoxycarbonyl)amino]methyl]-carboxycyclopropane serves as a key intermediate in the synthesis of agrochemicals. Its structural properties allow for the creation of compounds that can be used in pest control and crop protection, contributing to more effective and targeted agricultural solutions.
Used in Organic Chemistry Research and Development:
(1S,2S)-1-[[(N-tert-butoxycarbonyl)amino]methyl]-carboxycyclopropane is utilized as a valuable intermediate in organic chemistry research and development. Its unique stereochemistry and functional groups make it an essential component in the exploration of new synthetic pathways and the creation of novel organic compounds with potential applications across various industries.

Upstream product

• 167255-48-3 ((1R,2R)-2-Hydroxymethyl-cyclopropylmethyl)-carbamic acid tert-butyl ester 
• 173239-49-1 {(1S,2S)-2-[(trityloxy)methyl]cyclopropyl}methanol 
• 1449741-25-6 (1S,2S)-2-(triphenylmethoxymethyl)-1-(N-methoxy-N-methyl)carbamoylcycropropane 
• 1449741-24-5 (1S,2R)-2-(triphenylmethoxy)methyl-1-(N-methoxy-N-methyl)carbamoyl-1-phenylsulfonylcyclopropane 
• 409307-02-4 (1S,5R)-2-oxo-1-phenylsulfonyl-3-oxabicyclo[3.1.0]hexane 
• 1262755-28-1 N-tert-butoxycarbonyl[(1S,2S)-2-(aminomethyl)cyclopropyl]methanol 
• 253779-05-4 (1S,2S)-1-[[(N-tert-butoxycarbonyl)amino]methyl]-phenylcyclopropane 
• 1449741-28-9 (1R,2R)-1-(N-t-butoxycarbonyl)aminomethyl-2-(triphenylmethoxy)methylcyclopropane 
• 1449741-27-8 (1R,2R)-1-azidomethyl-2-(triphenylmethoxy)methylcyclopropane 
• 1449741-21-2 (1R,2R)-2-(triphenylmethoxymethyl)-1-(N-methoxy-N-methyl)carbamoylcycropropane 
• 142096-81-9 {(1R,2R)-2-[(trityloxy)methyl]cyclopropyl}methanol 
• 408348-28-7 (1R,5S)-1-(phenylsulfonyl)-3-oxabicyclo[3.1.0]hexan-2-one 
• 1449741-23-4 (1R,2S)-2-(triphenylmethoxy)methyl-1-(N-methoxy-N-methyl)carbamoyl-1-phenylsulfonylcyclopropane 
• 154001-57-7 tert-butyl-[(1R,2R)-2-((S)-2,2-dimethyl[1,3]dioxolan-4-yl)cyclopropylmethyl]diphenylsilane 

Relevant academic research and scientific papers

Cyclopropane-based conformational restriction of GABA by a stereochemical diversity-oriented strategy: Identification of an efficient lead for potent inhibitors of GABA transports

A series of cyclopropane-based conformationally restricted γ-aminobutyric acid (GABA) analogs with stereochemical diversity, that is, the trans- and cis-2,3-methano analogs Ia and Ib and their enantiomers ent-Ia and ent-Ib, and also the trans- and cis-3,4

An expedient asymmetric synthesis of N-protected (S, S)-2-aminomethyl-1- cyclopropanecarboxylic acid

An enantioselective synthesis of a N-Boc-protected trans-cyclopropane γ-amino acid is reported. The key chiral aldehyde intermediate is prepared in enantiomerically pure form using a three-step aldol-cyclopropanation-retro- aldol protocol.

A short stereoselective synthesis of a cyclopropyl analog of γ- aminobutyric acid (GABA)

An efficient synthesis of (S,S)-2-(aminomethyl) cyclopropane carboxylic acid has been achieved in 7 steps (38% overall yield) starting from commercially available cinnamyl alcohol. The synthesis involves initial stereoselective formation of the functional

Synthesis of Optically Active cis- and trans-1,2-Disubstituted Cyclopropane Derivatives by the Simmons-Smith Reaction of Allyl Alcohol Derivatives Derived from (R)-2,3-O-Isopropylideneglyceraldehyde

The Simmons-Smith reactions of Z- and E-allyl alcohol derivatives 6 derived from (R)-2,3-O-isopropylideneglyceraldehyde (5) were used for the synthesis of optically active cis- and trans-1,2-disubstituted cyclopropane derivatives.Reaction of 6 with diethyl zinc and diiodomethane gave cyclopropane derivatives 7 in 84percent to quantitative yields with 35 to ca. 100percent des.Identical facial selectivities toward the double bonds, 1re-2si for Z-6 and 1re-2re for E-6, were observed in the cyclopropanations.The diastereoselectivity was dependent on the protecting group on the terminal allylic oxygen (R of 6, TBDPS > MOM > Bn) and on the stereochemistry of the double bond (Z > E).For TBDPS ethers Z- and E-6c, cis- and trans-7c were obtained as single diastereomers, respectively.It was clearly demonstrated that the stereoselectivity of the cyclopropanation is controlled by the directing effect of the allylic oxygen (O-1) of the dioxolane ring, which coordinates to the reagent.The terminal allylic oxygen (O-2) lowered the diastereoselectivity.This reaction was applied to the synthesis of optically active cyclopropane analogs of γ-aminobutyric acid (GABA) 18, 22, and ent-22.