161111-13-3

Basic information

• Product Name: 3-Oxabicyclo[4.1.0]heptane-1-carboxylicacid,2-oxo-,(1R)-(9CI)
• Synonyms: 3-Oxabicyclo[4.1.0]heptane-1-carboxylicacid,2-oxo-,(1R)-(9CI)
• CAS NO: 161111-13-3
• Molecular Formula: C₇H₈O₄
• Molecular Weight: 156.14
• Product Categories: CARBOXYLICACID
• Mol File: 161111-13-3.mol
• Article Data: 1

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3-Oxabicyclo[4.1.0]heptane-1-carboxylicacid,2-oxo-,(1R)-(9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Oxabicyclo[4.1.0]heptane-1-carboxylicacid,2-oxo-,(1R)-(9CI)(161111-13-3)
• EPA Substance Registry System: 3-Oxabicyclo[4.1.0]heptane-1-carboxylicacid,2-oxo-,(1R)-(9CI)(161111-13-3)

Safety Data

• Hazardous Substances Data: 161111-13-3(Hazardous Substances Data)

Upstream product

• 161111-10-0 Di-tert-butyl (4-(benzyloxy)-(S)-2-(tosyloxy)butyl)malonate 
• 161111-11-1 Di-tert-butyl (R)-2-(2-(benzyloxy)ethyl)cyclopropane-1,1-dicarboxylate 
• 161111-12-2 Di-tert-butyl (R)-2-(2-hydroxyethyl)cyclopropane-1,1-dicarboxylate 

Downstream Products

• 161111-16-6 Methyl (1S,2R)-1--2-(2-(methanesulfonyloxy)ethyl)cyclopropanecarboxylate 
• 161111-17-7 (1S,2S)-1--1-(methoxycarbonyl)-2-(2-cyanoethyl)cyclopropane 
• 161111-15-5 Methyl (1S,2R)-1--2-(2-hydroxyethyl)cyclopropanecarboxylate 
• 1027841-26-4 (1S,2R)-1-Benzyloxycarbonylamino-2-(2-hydroxy-ethyl)-cyclopropanecarboxylic acid 
• 161111-14-4 (1S,6R)-1--3-oxabicyclo<4.1.0>-2-heptanone 
• 865375-33-3 methyl (1S,2S)-2-(2-azidoethyl)-1-{[(benzyloxy)carbonyl]amino}cyclopropanecarboxylate 

Relevant articles and documents

Synthesis of (1R,3R,5S)-1-amino-3-(hydroxymethyl)bicyclo[3.1.0]hexane as a precursor for the synthesis of carbocyclic nucleosides

The stereocontrolled synthesis has been achieved of a 1,5-methano-1-amino-5-(hydroxymethyl)cyclopentane, a potential component for carbocyclic nucleosides. Stereocontrol was manifest by converting (R)-2-((benzyloxy)ethyl)oxirane specifically to (2S,3S)-2-amino-2,3-methanoadipate through a series of lactones. This aminocyclopropanecarboxylate was then cyclized to the corresponding cyclopentanone ester. Reduction of the ketone, elimination, and hydrogenation of the double bond led primarily to the cyclopentane with the amino and ester groups trans (9/1). Enolization followed by an ammonium chloride quench then inverted this to a mixture in which the cis isomer was dominant (4/1). Simple functional group manipulation then gave the target (1R,3R,5S)-1-amino-3-(hydroxymethyl)bicyclo[3.1.0]hexane.