136522-35-5

Usage

Uses

Abacavir intermediate; antiviral therapeutic nucleoside analog.

InChI:InChI=1/C6H11NO/c7-6-2-1-5(3-6)4-8/h1-2,5-6,8H,3-4,7H2/t5-,6+/m1/s1

Upstream product

• 132243-27-7 cis-4-hydroxymethyl-1-ureidocyclopent-2-ene 
• 172720-97-7 (+/-)-tert-butyl (1RS,4SR)-4-(hydroxymethyl)cyclopent-2-enylcarbamate 
• 132243-26-6 2-carbamoyl-2-azabicyclo<2.2.1>hept-5-en-3-one 
• 130931-86-1 (-)-(1S,4R)-4-acetamidocyclopent-2-enylmethanol 
• 182689-66-3 ((1R,4S)-4-Hydroxymethyl-cyclopent-2-enyl)-carbamic acid methyl ester 
• 182689-48-1 Acetic acid (1S,4R,5S)-4-acetoxymethyl-5-tert-butoxy-cyclopent-2-enylmethyl ester 
• 127061-46-5 methyl (+)-cis-4-acetamidocyclopent-2-enecarboxylate 
• 1309768-09-9 (1S,4R)-methyl 4-azidocyclopent-2-enecarboxylate 
• 229177-39-3 1-amino-4-(hydroxymethyl)-2-cyclopentene 
• 229613-83-6 (–)-methyl (1S,4R)-4-aminocyclopent-2-ene-1-carboxylate hydrochloride 
• 130931-84-9 (-)-(1S,4R)-4-aminocyclopent-2-ene-1-carboxylic acid hydrochloride 
• 49805-30-3 2-azabicyclo[2.2.1.]hept-5-en-3-one 
• 182689-56-1 Acetic acid (1S,4R,5R)-5-tert-butoxy-4-hydroxymethyl-cyclopent-2-enylmethyl ester 
• 182689-61-8 Acetic acid (1S,4S,5S)-5-tert-butoxy-4-methoxycarbonylamino-cyclopent-2-enylmethyl ester 

Downstream Products

• 172720-97-7 (+/-)-tert-butyl (1RS,4SR)-4-(hydroxymethyl)cyclopent-2-enylcarbamate 
• 141271-11-6 (-)-(1S,4R)-4-<(2'-amino-6'-chloropyrimidin-4'-yl)amino>-cyclopent-2-enylmethanol 
• 168960-18-7 (1R,4S)-N-(tert-Butyloxycarbonyl)-1-amino-4-(hydroxymethyl)-2-cyclopentene 
• 216481-83-3 (+)-(1S,4R)-tert-butyl N-[4-(hydroxymethyl)-2-cyclopenten-1-yl]carbamate 
• 69971-20-6 (-)-(1S,4R) acetic acid 4-acetylamido-cyclopent-2-enyl-methyl ester 
• 136522-33-3 (1S,4R)-4-[2-amino-6-chloro-9H-purin-9-yl]-2-cyclopentene-1-methanol 
• 141271-13-8 (1S,4R)-4-(<2'-amino-6'-chloro-5'-<(4''-chlorophenyl)azo>pyrimidin-4'-yl>amino)cyclopent-2-enylmethanol 
• 172015-79-1 ((1S,4R)-4-(2-amino-6-chloro-9H-purin-9-yl)cyclopent-2-en-1-yl)methanol hydrochloride 
• 136470-78-5 abacavir 
• 141271-12-7 (1S, 4R)-(4-(2,5-diamino-6-chloro-4-pyrimidinyl)amino)-2-cyclopenten-1-methanol 
• 401796-85-8 (-)-(1S,4R)-1-monomethoxytrityloxymethyl-4-[(6'-monomethoxytritylaminopyrimidine-4'-yl)amino]cyclopent-2-ene 
• 859147-56-1 N-1-[(1R,4S)-4-{(monomethoxytrityl)oxymethyl}cyclopent-2-en-1-yl]-5'-O-{bis(phenylthio)phosphoryl}-2',3'-O-isopropylideneadenosine 
• 859147-52-7 N-1-[(1R,4S)-4-{(monomethoxytrityl)oxymethyl}cyclopent-2-en-1-yl]-5',O-(tert-butyldimethylsilyl)-2',3'-O-isopropylideneadenosine 
• 859147-54-9 N-1-[(1R,4S)-4-{(monomethoxytrityl)oxymethyl}cyclopent-2-en-1-yl]-2',3'-O-isopropylideneadenosine 

Relevant academic research and scientific papers

Synthesis of novel N-cyclopentenyl-lactams using the Aubé reaction

A novel and convenient method utilizing the Aubé reaction to access a new class of compounds that are similar to carbocyclic nucleosides is reported. The azido alcohol derived from Vince lactam undergoes the Aubé reaction with various cyclic ketones to gi

Acetoxy Meldrum's acid: A versatile acyl anion equivalent in the Pd-catalyzed asymmetric allylic alkylation

Acetoxy Meldrum's acid can serve as a versatile acyl anion equivalent in the Pd-catalyzed asymmetric allylic alkylation. The reaction of this nucleophile with various meso and racemic electrophiles afforded alkylated products in high yields and enantiopur

Synthesis of stable and cell-type selective analogues of cyclic ADP-ribose, a Ca2+-mobilizing second messenger. Structure-activity relationship of the N1-ribose moiety

We previously developed cyclic ADP-carbocyclic ribose (cADPcR, 2) as a stable mimic of cyclic ADP-ribose (cADPR, 1), a Ca2+-mobilizing second messenger. A series of the N1-ribose modified cADPcR analogues, designed as novel stable mimics of cAD

Process for the synthesis of chloropurine intermediates

The present invention relates to a process for the preparation of a carbocyclic purine nucleoside analogue of formula (I), its salts and pharmaceutically acceptable derivatives thereof which comprises hydrolysing a compound of formula (IV) wherein P is a protecting group, in the presence of an acid, condensing the product of formula (V) formed in situ in the presence of a base with a compound of formula (VI) followed by in situ ring closure of the resulting intermediate.

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.

Therapeutic nucleosides

The present invention relates to intermediates useful for the preparation of certain compounds, for example, purine carbocyclic nucleosides.

Synthesis of sugar-modified derivatives of the unusual nucleoside oxanosine and its carbocyclic analogs as potential inhibitors of HIV

The synthesis of sugar-modified derivatives of oxanosine and its carboxylic analogs was discussed. Natural oxanosine and (-)-2-azabicyclo[2.2.1]hept-5-en-3-one were used in the experiment and tested for an anti-HIV activities. Results showed a successful synthesis of sugar-modified derivatives of oxanosine and its carboxylic analogs for evaluation of their HIV-1 activity.

An efficient, scalable synthesis of the HIV reverse transcriptase inhibitor Ziagen (1592U89)

Ziagen, (1S, cis)-4-[2-amino-6-(cyclopropylamino)-9H-purin-9-yl]-2- cyclopentene-1-methanol, was synthesized from (1S,4R)-azabicyclo[2.2.1]hept- 5-en-3-one by efficient processes which bypass problematic steps in earlier routes. 2-Amino-4,6-dichloro-5-formamidopyrimidine is a key intermediate which makes possible an efficient construction of the purine from a chiral cyclopentenyl precursor.

Antiviral nucleoside analogues containing a substituted benzimidazole base attached to a carbocyclic ring

Antiviral purine nucleoside analogues contain a substituted benzimidazole base attached to a carbocyclic ring in place of the conventional sugar residue. Methods of treating herpes viral infections and pharmaceutical formulations are also described.