188885-85-0

Basic information

• Product Name: Bicyclo[3.1.0]hexane-6-carboxylic acid, 2-oxo-, ethyl ester, (1S,5R,6S)-
• CAS NO: 188885-85-0
• Molecular Formula: C9H12O3
• Molecular Weight: 168.192
• Mol File: 188885-85-0.mol
• Article Data: 10

Chemical Properties

• CAS DataBase Reference: Bicyclo[3.1.0]hexane-6-carboxylic acid, 2-oxo-, ethyl ester, (1S,5R,6S)-(CAS DataBase Reference)
• NIST Chemistry Reference: Bicyclo[3.1.0]hexane-6-carboxylic acid, 2-oxo-, ethyl ester, (1S,5R,6S)-(188885-85-0)
• EPA Substance Registry System: Bicyclo[3.1.0]hexane-6-carboxylic acid, 2-oxo-, ethyl ester, (1S,5R,6S)-(188885-85-0)

Safety Data

• Hazardous Substances Data: 188885-85-0(Hazardous Substances Data)

Upstream product

• 188885-82-7 ethyl (1SR,5RS,6SR)-2-oxobicyclo[3.1.0]hex-3-ene-6-carboxylate 
• 188885-73-6 (1R,2R,3R,5S,6S)-2,3-dihydroxy-4-oxobicyclo[3.1.0]hexane-6-carboxylic acid ethyl ester 
• 944282-70-6 (3aR,3bR,4S,4aS,5aR)-hexahydro-2,2-dimethyl-5-oxocyclopropa[3,4]cyclopenta[1,2-d]-1,3-dioxole-4-carboxylic acid ethyl ester 
• 115509-13-2 (3aR,6aR)-2,2-Dimethyl-3a,6a-dihydro-cyclopenta[1,3]dioxol-4-one 
• 1246564-20-4 2-hydroxy-bicyclo[3.1.0]hexane-6-carboxylic acid ethyl ester 
• 75-29-6 isopropyl chloride 
• 1246564-18-0 (1R,5S,6R,Rs)-1-(p-tolylsulfinyl)-2-oxobicyclo[3.1.0]hexane-6-carboxylate 
• 623-73-4 diazoacetic acid ethyl ester 
• 930-30-3 cyclopent-2-enone 
• 186541-47-9 (+)-(1S,5R,6S)-2-oxobicyclo[3.1.0]hexane-6-carboxylic acid 
• 5187-82-6 (ethoxycarbonylmethyl)dimethylsulfonium bromide 
• 176199-53-4 ethyl 2-oxobicyclo[3.1.0]hexane-6-carboxylate 
• 188885-79-2 C₁₁H₁₄O₄ 

Downstream Products

• 944282-71-7 (1S,3S,5R,6S)-3-[[3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-4-methoxyphenyl]hydroxymethyl]-2-oxobicyclo[3.1.0]hexane-6-carboxylic acid ethyl ester 
• 944282-72-8 (1S,3S,5R,6S)-3-[[3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-4-methoxyphenyl]methyl]-2-oxobicyclo[3.1.0]hexane-6-carboxylic acid ethyl ester 
• 176199-48-7 eglumetad 
• 234085-19-9 (1S, 2S, 3S, 5R, 6S)-2-amino-3-fluorobicyclo[3.1.0]hexane-2,6-dicarboxylic acid 
• 944282-74-0 2,2-dimethylpropanoic acid [(1S,3S,5R,6S)-3-[[3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-4-methoxyphenyl]methyl]-2-oxobicyclo[3.1.0]hexan-6-yl]methyl ester 
• 944282-73-9 C₂₁H₃₄O₄Si 

Relevant articles and documents

Asymmetric synthesis of (+)-2-aminobicyclo[3.1.0]hexane-2,6-dicarboxylic acid (LY354740)

The assymetric synthesis of (+)-2-aminobicyclo[3.1.0]hexane-2,6-dicarboxylic acid (LY354740) 1, a potent and selective group 2 mGluR agonist, has been accomplished starting from the readily available enantiomerically pure cyclopentenone 4. Thus, cyclopropanation with ethyl(dimethylsulfuranylidene)acetate generated in situ with DBU, followed by deketalization gave rise to the dihydroxy bicyclic ketone 9. After protecting the ketone as 1,3-dioxolane and its transformation to the orthoformate 11, this was pyrolytically deoxygenated in a sealed tube to the bicyclic enone 13. The synthesis was completed after hydrogenation, stereoselective Bucherer-Bergs reaction and hydantoin hydrolysis, yielding LY354740 (+)-1 with an e.e. ≤98%. reserved.

Constrained cycloalkyl analogues of glutamic acid: Stereocontrolled synthesis of (+)-2-aminobicyclo[3.1.0]hexane-2,6-dicarboxylic acid (LY354740) and its 6-phosphonic acid analogue

A new stereocontrolled synthesis of (+)-2-aminobicyclo[3.1.0]hexane-2.6- dicarboxylic acid (LY354740) 1, a potent and selective 2mGluR agonist, has been accomplished in four steps with an overall yield of 27% starting from the enantiopure (+)-(R)-2-(p-tolylsulfinyl)cyclopent-2-enone 3. The key steps include asymmetric cyclopropanation of 3 with (dimethylsulfuranylidene)acetate (EDSA) and removal of the chiral p-tolylsulfinyl auxiliary from the cycloadduct ent-4c upon treatment with iso-propylmagnesium chloride. The stereoselective hydantoin formation from the bicyclic ketone 6 formed (Bucherer-Bergs reaction) and subsequent hydrolysis completed the synthesis of 1. The same reaction sequence has been applied in the first synthesis of enantiopure (+)-2-amino-6-phosphonobicyclo[3.0.1]hexane-2-carboxylic acid 2, a structural 6-phosphono analogue of 1. The starting bicyclic ketophosphonates 9-11 have been obtained by asymmetric cyclopropanation of (-)-(S)-3 with phosphoryl sulfonium ylides, producing only two endo-isomers. The major endo-isomer (+)-11a containing the 6-diisopropoxyphosphoryl group has been converted in three steps into (+)-endo-2 in 46% overall yield.

Synthesis of the otteliones A and B: Use of a cyclopropyl group as both a steric shield and a vinyl equivalent

(Chemical Equation Presented) To A and B: The extremely powerful antitumor agents ottelione A and B have been synthesized from D-ribose. Key steps in the synthesis involve the use of a cyclopropane unit fused onto a five-membered ring to control the stere