268737-90-2

Basic information

• Product Name: [4S,2R,3R]-(4-benzyl-2-thioxooxazolidin-3-yl)(2-hydroxycyclopent-3-enyl)methanone
• Synonyms: [4S,2R,3R]-(4-benzyl-2-thioxooxazolidin-3-yl)(2-hydroxycyclopent-3-enyl)methanone
• CAS NO: 268737-90-2
• Molecular Weight: 303.382
• Mol File: 268737-90-2.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: [4S,2R,3R]-(4-benzyl-2-thioxooxazolidin-3-yl)(2-hydroxycyclopent-3-enyl)methanone(CAS DataBase Reference)
• NIST Chemistry Reference: [4S,2R,3R]-(4-benzyl-2-thioxooxazolidin-3-yl)(2-hydroxycyclopent-3-enyl)methanone(268737-90-2)
• EPA Substance Registry System: [4S,2R,3R]-(4-benzyl-2-thioxooxazolidin-3-yl)(2-hydroxycyclopent-3-enyl)methanone(268737-90-2)

Safety Data

• Hazardous Substances Data: 268737-90-2(Hazardous Substances Data)

Upstream product

• 318488-35-6 (E)-(2S,3R)-2-Allyl-1-((R)-4-benzyl-2-thioxo-oxazolidin-3-yl)-3-hydroxy-hex-4-en-1-one 
• 268737-88-8 4R-1-(4-benzyl-2-thiooxazolidin-3-yl)pent-4-en-1-one 
• 268737-89-9 (2S,3R)-2-Allyl-1-((R)-4-benzyl-2-thioxo-oxazolidin-3-yl)-3-hydroxy-pent-4-en-1-one 

Downstream Products

• 136522-33-3 (1S,4R)-4-[2-amino-6-chloro-9H-purin-9-yl]-2-cyclopentene-1-methanol 
• 136470-78-5 abacavir 
• 268737-92-4 Benzoic acid (1R,5R)-5-(tert-butyl-dimethyl-silanyloxymethyl)-cyclopent-2-enyl ester 
• 268737-86-6 cis-3-benzoyloxy-4-(hydroxymethyl)cyclopentene 

Relevant articles and documents

An efficient, general asymmetric synthesis of carbocyclic nucleosides: Application of an asymmetric aldol/ring-closing metathesis strategy

A general and efficient synthesis of carbocyclic and hexenopyranosyl nucleosides has been developed. The strategy combines three key transformations: an asymmetric aldol addition to establish the relative and absolute configuration of the pseudosugar, a ring-closing metathesis to construct the pseudosugar ring, and a Trost-type palladium(0)-mediated substitution to assemble the pseudosugar and the aromatic base. Carbovir, abacavir, and their 2'-methyl derivatives as well as hexenopyranosyl nucleoside analogues have been prepared by this sequence.