147332-45-4

Basic information

• Product Name: 2-Cyclopentene-1-methanol, 4-(6-amino-9H-purin-9-yl)-, (1S,4R)-
• CAS NO: 147332-45-4
• Molecular Formula: C11H13N5O
• Molecular Weight: 231.257
• Mol File: 147332-45-4.mol

Chemical Properties

• CAS DataBase Reference: 2-Cyclopentene-1-methanol, 4-(6-amino-9H-purin-9-yl)-, (1S,4R)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Cyclopentene-1-methanol, 4-(6-amino-9H-purin-9-yl)-, (1S,4R)-(147332-45-4)
• EPA Substance Registry System: 2-Cyclopentene-1-methanol, 4-(6-amino-9H-purin-9-yl)-, (1S,4R)-(147332-45-4)

Safety Data

• Hazardous Substances Data: 147332-45-4(Hazardous Substances Data)

Upstream product

• 66224-66-6 adenine 
• 143643-01-0 (R)-4-Benzyloxymethyl-cyclopent-2-enone 
• 143643-00-9 (1R,4S)-4-Benzyloxymethyl-cyclopent-2-enol 
• 137836-49-8 Acetic acid (1R,4S)-4-(6-amino-purin-9-yl)-cyclopent-2-enylmethyl ester 

Downstream Products

• 13190-75-5 (+/-)-C-Adenosine 
• 72346-00-0 (+/-)-9-<2α,3α-dihydroxy-4α-(hydroxymethyl)cyclopent-1α-yl>adenine 
• 112966-73-1 [(1R,3S)-3-(6-amino-9H-purin-9-yl)cyclopentyl]methanol 
• 19186-33-5 aristeromycin 

Relevant articles and documents

A Novel, One-Pot Ring Expansion of Cyclobutanones. Syntheses of Carbovir and Aristeromycin

A novel, one-pot ring-expansion procedure was developed using Me3S(O)I, NaH, and Sc(OTf)3. The scope and limitations were briefly examined, and a tentative mechanism was proposed. Application of the methodology to known cyclobutanone 1 provided the corresponding cyclopentanone, which was successfully advanced to (+)-carbovir and (+)-aristeromycin.

Synthesis of (+/-)-2',3'-Didehydro-2',3'-dideoxy Nucleosides via a Modified Prins Reaction and Palladium(0) Catalysed Coupling

Cyclopentenyl allylic acetates have been prepared in diastereoisomerically enriched form by modification of the Prins reaction.Palladium(0) catalysed coupling between these allylic acetates and a heteroaromatic base provides a highly convergent and direct route for synthesising carbocyclic 2',3'-didehydro-2',3'-dideoxy nucleosides.The method is exemplified by the coupling reaction with adenine which yields (+/-)-2',3'-didehydro-2',3'-dideoxyaristeromycin 5'-O-acetate 22 in 50percent yield.This has been converted in two steps into (+/-)-aristeromycin triacetate 5.