136522-35-5

Basic information

• Product Name: (1S-cis)-4-Amino-2-cyclopentene-1-methanol
• Synonyms: (1s-cis)-4-amino-2-cyclopentene-1-methanol;(1s,4r)-4-amino-2-cyclopentene-1-methanol;Aminocarbinol [(1S.Cis)-4-amino-2-cyclopenten-1-methanol];(1S,4R)-cis-4-Amino-2-cyclopentene-1-methanol;((1S,4R)-4-aminocyclopent-2-enyl)methanol;REF DUPL: (1S-cis)-4-Amino-2-cyclopentene-1-methanol;(1S,4R)-cis-4-Amino-2-cyclopentene-1-methano;[(1R,4S)-4-Aminocyclopent-2-en-1-yl]methanol
• CAS NO: 136522-35-5
• Molecular Formula: C₆H₁₁NO
• Molecular Weight: 113.15764
• EINECS: 200-258-5
• Product Categories: Chiral Reagents;Bases & Related Reagents;Intermediates;Nucleotides
• Mol File: 136522-35-5.mol
• Article Data: 19

Chemical Properties

• Boiling Point: 203°C
• Flash Point: 77°C
• Appearance: /
• Density: 1.046
• Vapor Pressure: 0.068mmHg at 25°C
• Refractive Index: 1.512
• PKA: 14.86±0.10(Predicted)
• CAS DataBase Reference: (1S-cis)-4-Amino-2-cyclopentene-1-methanol(CAS DataBase Reference)
• NIST Chemistry Reference: (1S-cis)-4-Amino-2-cyclopentene-1-methanol(136522-35-5)
• EPA Substance Registry System: (1S-cis)-4-Amino-2-cyclopentene-1-methanol(136522-35-5)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36/37/38
• Safety Statements: 26
• Hazardous Substances Data: 136522-35-5(Hazardous Substances Data)

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 
• 229177-39-3 1-amino-4-(hydroxymethyl)-2-cyclopentene 
• 1309768-09-9 (1S,4R)-methyl 4-azidocyclopent-2-enecarboxylate 
• 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 
• 127061-46-5 methyl (+)-cis-4-acetamidocyclopent-2-enecarboxylate 
• 49805-30-3 2-azabicyclo[2.2.1.]hept-5-en-3-one 
• 182689-48-1 Acetic acid (1S,4R,5S)-4-acetoxymethyl-5-tert-butoxy-cyclopent-2-enylmethyl ester 
• 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 
• 1026493-16-2 (1S,4S,5S)-4-Acetoxymethyl-5-tert-butoxy-cyclopent-2-enecarboxylic acid 
• 182689-64-1 Acetic acid (1S,4R)-4-methoxycarbonylamino-cyclopent-2-enylmethyl ester 
• 182689-49-2 ((1S,4R,5S)-5-tert-Butoxy-4-hydroxymethyl-cyclopent-2-enyl)-methanol 
• 151792-53-9 tert-butyl (1R,4S)-(-)-3-oxo-2-azabicyclo[2.2.1]hept-5-ene-2-carboxylate 

Downstream Products

• 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 
• 172720-97-7 (+/-)-tert-butyl (1RS,4SR)-4-(hydroxymethyl)cyclopent-2-enylcarbamate 
• 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 articles and documents

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

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 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.