172721-00-5

Basic information

• Product Name: [4(R)-(2-amino-6-chloropurine-9-yl)-cyclopent-2-ene-l(S)-yl]methanol
• CAS NO: 172721-00-5
• Molecular Weight: 265.702
• Mol File: 172721-00-5.mol
• Article Data: 34

Chemical Properties

• CAS DataBase Reference: [4(R)-(2-amino-6-chloropurine-9-yl)-cyclopent-2-ene-l(S)-yl]methanol(CAS DataBase Reference)
• NIST Chemistry Reference: [4(R)-(2-amino-6-chloropurine-9-yl)-cyclopent-2-ene-l(S)-yl]methanol(172721-00-5)
• EPA Substance Registry System: [4(R)-(2-amino-6-chloropurine-9-yl)-cyclopent-2-ene-l(S)-yl]methanol(172721-00-5)

Safety Data

• Hazardous Substances Data: 172721-00-5(Hazardous Substances Data)

Usage

Uses

trans-4-(2-Amino-6-chloro-9H-purin-9-yl)-2-cyclopentene-1-methanol is an intermediate in the synthesis of trans-isomer of Abacavir (A104990), a nucleoside reverse transcriptase inhibitor (NRTI) (1).

Upstream product

• 134628-02-7 cis-(+/-)-4-(2-Amino-6-chloro-9H-purin-9-yl)-2-cyclopenten-1-yl methyl carbonate 
• 72656-82-7 anti-3-(Hydroxymethyl)-6-oxabicyclo<3.1.0>hexane 
• 86885-57-6 trans-3-carbomethoxy-6-oxabicyclo<3.1.0>hexane 
• 160081-33-4 (1S,4S)-trans-4-tert-butyldimethylsiloxymethyl-2-cyclopenten-1-ol 
• 130931-86-1 (-)-(1S,4R)-4-acetamidocyclopent-2-enylmethanol 
• 127061-46-5 methyl (+)-cis-4-acetamidocyclopent-2-enecarboxylate 
• 79200-56-9 (-)-2-azabicyclo[2.2.1]hept-5-en-3-one 
• 141271-13-8 (1S,4R)-4-(<2'-amino-6'-chloro-5'-<(4''-chlorophenyl)azo>pyrimidin-4'-yl>amino)cyclopent-2-enylmethanol 
• 122-51-0 orthoformic acid triethyl ester 
• 61865-49-4 ester methylique de l'acide (acetamido-cis-4)-cyclopentene-2-carboxylique 
• 171887-03-9 N-(2-amino-4,6-dichloropyrimidin-5-yl)formamide 
• 137782-35-5 (+)-cis-2-amino-6-chloro-9'-<(4'R)-(triphenylmethoxymethyl)cyclopent-2'-en-(1'S)-yl>purine 
• 122624-75-3 (+/-)-cis-<4-<<2-amino-6-chloro-5-<(4-chlorophenyl)azo>-4-pyrimidinyl>amino>-2-cyclopentenyl>carbinol 
• 61865-50-7 Acetic acid 4-acetylamino-cyclopent-2-enylmethyl ester 

Downstream Products

• 118353-05-2 (+/-)-cis-2-amino-1,9-dihydro-9-[4-(hydroxymethyl)-2-cyclopenten-1-yl]-6H-purin-6-one 

Relevant articles and documents

A new nucleophilic ring opening of an activated cyclopropane and a formal synthesis of (+/-)-carbovir.

The reaction of bicyclo[3.1.0]hexane 1, possessing a doubly activated cyclopropane ring, with acetic acid and potassium acetate in DMSO proceeded smoothly to give the adduct 2 in good yield. A formal total synthesis of the potent anti-HIV agent (+/-)-carb

ANTIVIRAL 4-(2-AMINO-6-HETEROCYLYL-9H-PURIN-9-YL)-2-CYCLOPENTENE-1 -METHANOL COMPOUNDS

The present invention relates to certain antiviral compounds of formula I as defined herein that function as nucleoside reverse transcriptase inhibitors. The present invention also relates to processes for the preparation of these compounds, pharmaceutical compositions comprising them and to their use for the treatment of retroviral infections, and in particular their use in the treatment of HIV-1 virus.

Enantioselective syntheses of carbanucleosides from the Pauson-Khand adduct of trimethylsilylacetylene and norbornadiene

(Chemical Equation Presented) A new enantioselective approach to carbanucleosides from Pauson-Khand (PK) adduct 1 is disclosed. The chiral cyclopentenone 1 is readily accessible in enantiomerically pure form via PK reaction of trimethylsilylacetylene and norbornadiene using N-benzyl-N- diphenylphosphino-tert-butyl-sulfinamide as a chiral P,S ligand. (-)-Carbavir and (-)-Abacavir were enantioselectively synthesized starting from (-)-1. The key steps of the sequence are a photochemical conjugate addition of a hydroxymethyl radical, a retro-Diels-Alder reaction, and a palladium catalyzed allylic substitution to introduce the nucleobase.

Process for the preparation of aminoalcohol derivatives and their further conversion to (1R, 4S)-4-((2-amino-6-chloro-5-formamido-4-pyrimidinyl)-amino)-2-cyclopentenyl-1- methanol

The invention relates to a novel process for the preparation of an aminoalcohol of the formula 1racemically or optically active, starting from 2-azabi-cyclo[2.2.1]hept-5-en-3-one, its further conversion to give the corresponding acyl derivative and its further conversion to (1S,4R)- or (1R,4S)-4-(2-amino-6-chloro-9-H-purine-9-yl)-2-cyclopentenyl-1-methanol of the formulae 2In the latter synthesis, the aminoalcohol is converted into the corresponding D- or L-tartrate, which is then reacted with N-(2-amino-4,6-dichloropyrimidin-5-yl) formamide of the formula 3to give (1S,4R)- or (1R,4S)-4-[(2-amino-6-chloro-5-formamido-4-pyrimidinyl)amino]-2-cyclopentenyl-1-methanol of the formulae 4and then cyclized to give the end compounds.