176027-90-0

Basic information

• Product Name: Bicyclo[3.1.0]hexane-2,6-dicarboxylic acid, 2-amino-, (1R,2R,5S,6R)-rel- (9CI)
• Synonyms: Bicyclo[3.1.0]hexane-2,6-dicarboxylic acid, 2-amino-, (1R,2R,5S,6R)-rel- (9CI);VTAARTQTOOYTES-RGDLXGNYSA-N
• CAS NO: 176027-90-0
• Molecular Formula: C8H11NO4
• Molecular Weight: 185.17724
• Product Categories: CYCLOPENTANE
• Mol File: 176027-90-0.mol
• Article Data: 10

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Bicyclo[3.1.0]hexane-2,6-dicarboxylic acid, 2-amino-, (1R,2R,5S,6R)-rel- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Bicyclo[3.1.0]hexane-2,6-dicarboxylic acid, 2-amino-, (1R,2R,5S,6R)-rel- (9CI)(176027-90-0)
• EPA Substance Registry System: Bicyclo[3.1.0]hexane-2,6-dicarboxylic acid, 2-amino-, (1R,2R,5S,6R)-rel- (9CI)(176027-90-0)

Safety Data

• Hazardous Substances Data: 176027-90-0(Hazardous Substances Data)

Usage

Uses

LY 354740 is an analog of glutamate and a highly potent, efficacious and selective group II (mGlu2/3) receptor agonist (1,2,3). Compounds that target at mGlu receptors may be useful for treating anxiety-related disorders.

Upstream product

• 188885-79-2 C₁₁H₁₄O₄ 
• 188885-85-0 (1S,5R,6S)-2-oxo-bicyclo[3.1.0]hexane-6-carboxylic acid ethyl ester 
• 188885-82-7 ethyl (1SR,5RS,6SR)-2-oxobicyclo[3.1.0]hex-3-ene-6-carboxylate 
• 219762-23-9 C₁₈H₂₅NO₇ 
• 219762-17-1 C₁₆H₂₁Cl₃O₅ 
• 219762-19-3 C₁₆H₂₁N₃O₆ 
• 219762-21-7 C₁₆H₂₃NO₆ 
• 219762-26-2 (1R,1aR,1bR,4aS,5R,5aS)-5-Acetylamino-3-ethoxy-hexahydro-2,4-dioxa-cyclopropa[a]pentalene-1,5-dicarboxylic acid dimethyl ester 
• 219762-25-1 (1S,2R,3S,4R,5R,6R)-2-Acetylamino-3,4-dihydroxy-bicyclo[3.1.0]hexane-2,6-dicarboxylic acid dimethyl ester 
• 219762-27-3 (1S,2S,5R,6S)-2-Acetylamino-bicyclo[3.1.0]hex-3-ene-2,6-dicarboxylic acid dimethyl ester 
• 188885-69-0 C₁₅H₂₀O₅ 
• 597540-60-8 (2aR,2bR,4aS,4bS)-1-(4-Methoxy-benzyl)-2-oxo-hexahydro-1-aza-cyclopropa[cd]pentalene-4a-carboxylic acid methyl ester 
• 488859-10-5 (1S,2S,5R,6S)-2-tert-butoxycarbonylaminobicyclo[3.1.0]hexane-2,6-dicarboxylic acid 6-methyl ester 
• 597540-63-1 (1S,2S,5R,6R)-2-tert-Butoxycarbonylamino-bicyclo[3.1.0]hexane-2,6-dicarboxylic acid dimethyl ester 

Relevant articles and documents

Enantiospecific synthesis of (1S,2S,5R,6S)-2-aminobicyclo[3.1.0]hexane- 2,6-dicarboxylic acid by a modified Corey-Link reaction

(1S,2S,5R,6S)-2-Aminobicyclo[3.1.0]hexane-2,6-dicarboxylic acid (LY354740) was synthesised enantiospecifically from a sugar derived enantiomerically pure cyclopentenone. The α-amino acid stereogenic centre was formed by reacting the ketone with chloroform anion and then the alcohol so formed was reacted with sodium azide/DBU in methanol to give an azido ester. Critically, this modified Corey-Link reaction gives the opposite stereochemical outcome to the traditional Bucherer-Bergs and Strecker reactions. The azide was reduced and acylated, the 1,2 diol deoxygenated and the protecting groups removed to give LY354740 with an e.e.>98%.

Stereocontrolled synthesis of a potent agonist of group II metabotropic glutamate receptors, (+)-LY354740, and its related derivatives

Efficient synthesis of (+)-2-aminobicyclo[3.1.0]hexane-2,6-dicarboxylic acid (LY354740: 1) and its structurally related analogs (-)-2 and (-)-3 has been accomplished starting with (1S,2R)-1-amino-2-hydroxycyclopentane- or cyclohexanecarboxylic acid (4 or 17 ) via an intramolecular cyclopropanation of α-diazo acetamide.

Preparation of bicyclohexane derivative

A process for the preparation of (+)-2-amino-bicyclo[3.1.0]-hexane-2-6-dicarboxylic acid, or a pharmaceutically acceptable salt thereof, which comprises hydrolysing (-)-2-spiro-5''-hydantoinbicyclo[3.1.0]hexane-6-carboxylic acid or a salt thereof, and optionally forming a pharmaceutically acceptable salt. Also disclosed are intermediates useful in the process.