117857-96-2

Basic information

• Product Name: (2S,3R,4S)-CCG
• Synonyms: (2S,3R,4S)-CCG;(2S,3R,4S)-ALPHA-(CARBOXYCYCLOPROPYL)GLYCINE;(2S,1'R,2'S)-2-(CARBOXYCYCLOPROPYL)GLYCINE;L-CCG-IV;(2S,3R,4S)-A-(CARBOXYCYCLOPROPYL)GLYCINE POTENT NMDA RECEPTOR;(1S,2R)-2-[(1S)-1-Amino-2-oxo-2-hydroxyethyl]cyclopropane-1-carboxylic acid;(2S)-2-Amino-2-[(1R,2S)-2-carboxycyclopropan-1-yl]acetic acid;2-[(1R,2S)-2-(Carboxy)cyclopropyl]-L-glycine
• CAS NO: 117857-96-2
• Molecular Formula: C6H9NO4
• Molecular Weight: 159.14
• Mol File: 117857-96-2.mol
• Article Data: 13

Chemical Properties

• Appearance: off-white/solid
• Solubility: H2O: soluble
• CAS DataBase Reference: (2S,3R,4S)-CCG(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,3R,4S)-CCG(117857-96-2)
• EPA Substance Registry System: (2S,3R,4S)-CCG(117857-96-2)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 117857-96-2(Hazardous Substances Data)

Upstream product

• 128134-29-2 2-((R)-Benzyloxycarbonylamino-methoxycarbonyl-methyl)-cyclopropanecarboxylic acid ethyl ester 
• 117747-68-9 (1S,2S)-2-((S)-1-tert-Butoxycarbonylamino-2-hydroxy-ethyl)-cyclopropanecarboxylic acid ethyl ester 
• 167937-05-5 (1S,2S)-2-((S)-tert-Butoxycarbonylamino-carboxy-methyl)-cyclopropanecarboxylic acid 
• 206192-90-7 C-[(S)-C-Furan-2-yl-C-((1S,2S)-2-furan-2-yl-cyclopropyl)]-methylamine 
• 42811-85-8 (E)-1,3-bis(furan-2-yl)-2-propen-1-one 
• 197787-42-1 (1S,2S)-2-((S)-1-tert-Butoxycarbonylamino-2-hydroxy-ethyl)-cyclopropanecarboxylic acid tert-butyl ester 
• 117747-68-9 (S)-2-((S)-1-tert-Butoxycarbonylamino-2-hydroxy-ethyl)-cyclopropanecarboxylic acid ethyl ester 
• 124085-73-0 (2S)-N-(tert-Butoxycarbonyl)-2-((ethoxycarbonyl)-cyclopropyl)glycinol 
• 128134-31-6 (R)-4-[(R)-2-((R)-2-Hydroxy-1-phenyl-ethylcarbamoyl)-cyclopropyl]-5-oxo-oxazolidine-3-carboxylic acid benzyl ester 
• 129569-91-1 (1S,2S)-2-((R)-tert-Butoxycarbonylamino-carboxy-methyl)-cyclopropanecarboxylic acid 
• 206192-93-0 C-[(R)-C-Furan-2-yl-C-((1S,2S)-2-furan-2-yl-cyclopropyl)]-methylamine 
• 129569-16-0 (1S,2S)-2-((R)-1-tert-Butoxycarbonylamino-2-hydroxy-ethyl)-cyclopropanecarboxylic acid ethyl ester 
• 124085-73-0 2-[(R)-1-tert-Butoxycarbonylamino-2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-cyclopropanecarboxylic acid ethyl ester 
• 128134-30-5 (R)-4-(2-Carboxy-cyclopropyl)-5-oxo-oxazolidine-3-carboxylic acid benzyl ester 

Downstream Products

• 128134-30-5 (R)-4-(2-Carboxy-cyclopropyl)-5-oxo-oxazolidine-3-carboxylic acid benzyl ester 
• 22255-17-0 (2R,3R,4R) α-(Carboxycyclopropyl)glycine 
• 22255-17-0 (2R,3S,4S) α-(Carboxycyclopropyl)glycine 
• 128134-31-6 (R)-4-[(R)-2-((R)-2-Hydroxy-1-phenyl-ethylcarbamoyl)-cyclopropyl]-5-oxo-oxazolidine-3-carboxylic acid benzyl ester 
• 128134-31-6 (R)-4-[(S)-2-((R)-2-Hydroxy-1-phenyl-ethylcarbamoyl)-cyclopropyl]-5-oxo-oxazolidine-3-carboxylic acid benzyl ester 

Relevant articles and documents

Novel stereocontrolled approach to conformationally constrained analogues of L-glutamic acid and L-proline via stereoselective cyclopropanation of 3,4-didehydro-L-pyroglutamic ABO ester

A new stereocontrolled approach to l-(carboxycyclopropyl)glycines (l-CCGs) and 3,4-methano-l-prolines, conformationally constrained analogues of l-glutamic acid and l-proline, respectively, was developed using a 3,4-didehydro-l- pyroglutamate derivative as a common chiral template. The unsaturated l-pyroglutamate derivative employed in this work is a novel chiral synthon in which the carboxyl functionality is protected as a 2,7,8-trioxabicyclo[3.2.1] octyl group (ABO ester). Stereospecific cyclopropanation of the olefin using diazomethane followed by appropriate functional group interconversion gave l-CCG-III and trans-3,4-methano-l-proline with complete stereocontrol. Synthesis of other diastereomers of l-CCG and cis-3,4-methano-l-proline was accomplished by alteration of the 3,4-methanoglutamic acid framework via carboxycyclopropanation of the olefin with sulfur ylide and subsequent Barton decarboxylation reaction of the original γ-carboxyl group included in the pyroglutamate skeleton.

Novel enantioselective synthesis of trans-α-(2-carboxycyclo-prop-1- yl)glycines: Conformationally constrained L-glutamate analogues

D- and L-α-(2-carboxycycloprop-1-yl)glycines were synthesized from trans-1,3-di(2-furyl)propenone. Conversion of the double bond to a cyclopropane is followed by the formation of an oxime ether. Enantioselective reduction of the oxime ether, separation of diastereomers and oxidation of the furane rings gave enantiomerically pure D- and L-CCG I and CCG II. The structure of oxime 7b was determined by X-ray crystal structure analysis. The key step is the oxazaborolidine catalyzed enantioselective conversion of oxime ethers to amines.

Study of the reactivity profile of glycine Schiff's bases with dipolarophiles: Application towards a concise synthesis of CCG-II

The reactivity profile of glycine Schiff's bases with crotonate and bromocrotonate has been shown to take a different course depending on the choice substituent on the imine. Application of the above study for the mild and concise synthesis of CCG-II has been achieved.