142187-88-0

Basic information

• Product Name: 9-(4,5-bishydroxymethylcyclopent-2-en-1-yl)-9H-adenine
• Synonyms: 9-(4,5-bishydroxymethylcyclopent-2-en-1-yl)-9H-adenine
• CAS NO: 142187-88-0
• Molecular Formula: C12H15 N5 O2
• Molecular Weight: 0
• Mol File: 142187-88-0.mol

Chemical Properties

• Boiling Point: 556.2°Cat760mmHg
• Flash Point: 290.2°C
• Appearance: /
• Density: 1.66g/cm³
• Vapor Pressure: 3.32E-13mmHg at 25°C
• Refractive Index: 1.8
• CAS DataBase Reference: 9-(4,5-bishydroxymethylcyclopent-2-en-1-yl)-9H-adenine(CAS DataBase Reference)
• NIST Chemistry Reference: 9-(4,5-bishydroxymethylcyclopent-2-en-1-yl)-9H-adenine(142187-88-0)
• EPA Substance Registry System: 9-(4,5-bishydroxymethylcyclopent-2-en-1-yl)-9H-adenine(142187-88-0)

Safety Data

• Hazardous Substances Data: 142187-88-0(Hazardous Substances Data)

Usage

InChI:InChI=1/C12H15N5O2/c13-11-10-12(15-5-14-11)17(6-16-10)9-2-1-7(3-18)8(9)4-19/h1-2,5-9,18-19H,3-4H2,(H2,13,14,15)/t7-,8-,9-/m0/s1

Upstream product

• 143572-32-1 [(1R,2R,5S)-2-(6-Chloro-purin-9-yl)-5-hydroxymethyl-cyclopent-3-enyl]-methanol 
• 140440-30-8 7-syn-<(benzyloxy)methyl>-2-azabicyclo<2.2.1>hept-5-en-3-one 
• 140440-36-4 (+/-)-5-amino-4-<<5'α-<(benzyloxy)methyl>-4'β-(hydroxymethyl)cyclopent-2'-en-1'β-yl>amino>-6-chloropyrimidine 
• 140440-33-1 7-syn-<(benzyloxy)methyl>-2-(ethoxycarbonyl)-2-azabicyclo<2.2.1>hept-5-en-3-one 
• 140440-35-3 (+/-)-5α-<(benzyloxy)methyl>-4β-(hydroxymethyl)cyclopent-2-en-1β-ylamine 
• 117624-93-8 (3aS,4R,5S,6aR)-5-(tert-Butyl-dimethyl-silanyloxy)-4-(tert-butyl-dimethyl-silanyloxymethyl)-hexahydro-cyclopenta[b]furan-2-one 
• 143833-71-0 (1R,2S,3R,4S)-4-(tert-Butyl-dimethyl-silanyloxy)-3-(tert-butyl-dimethyl-silanyloxymethyl)-2-(2-hydroxy-ethyl)-cyclopentanol 
• 143833-72-1 (1R,2S,3R,4S)-4-(tert-Butyl-dimethyl-silanyloxy)-3-(tert-butyl-dimethyl-silanyloxymethyl)-2-vinyl-cyclopentanol 
• 143833-70-9 Acetic acid (1S,5S,6S,8R)-6-bromo-3-oxo-2-oxa-bicyclo[3.2.1]oct-8-ylmethyl ester 
• 54423-47-1 (+/-)-(3aα,4α,5β,6aα)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopentafuran-2-one 
• 143833-79-8 Acetic acid (1R,2R,5S)-2-(6-chloro-purin-9-yl)-5-hydroxymethyl-cyclopent-3-enylmethyl ester 
• 140440-38-6 (+/-)-9-<5'α-<(benzyloxy)methyl>-4'β-(hydroxymethyl)cyclopent-2'-en-1'β-yl>adenine 
• 143572-31-0 9-[(1R,4S,5R)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-4-(tert-butyl-diphenyl-silanyloxymethyl)-cyclopent-2-enyl]-6-chloro-9H-purine 
• 130386-85-5 (3aR,4S,5R,6aS)-5-benzoyloxy-4-[(t-butyldiphenylsiloxy)methyl]hexahydro-2H-cyclopenta[b]furan-2-one 

Relevant articles and documents

Synthesis of nucleosides and related compounds. XXXI. Resolution of 9-[c- 4, t-5-bis(hydroxymethyl)cyclopent-2-en-r-1-yl]-9H-adenine [(±)-BCA] by means of high-pressure-mediated deamination with adenosine deaminase

Deamination of an anti-human immunodeficiency virus (anti-HIV) carbocyclic adenine nucleoside, 9-[c-4,t-5-bis(hydroxymethyl)cyclopent-2-en-r-1-yl]-9H- adenine (BCA) by adenosine deaminase under a variety of pressures (1 bar- 6kbar) was investigated. It was found that, while (+)-BCA was practically unaffected, the deamination of (-)-BCA was remarkably enhanced under 4 kbar to give the corresponding (-)-hypoxanthine derivative [(-)-BCH)] in nearly 100% ee.

Chemoenzymatic synthesis of antiviral carbocyclic nucleosides: Asymmetric hydrolysis of meso-3,5-bis(acetoxymethyl)cyclopentenes using Rhizopus delemar lipase

7-Substituted norbornadienes were stereoselectively converted into the meso-3,5-bis(acetoxymethyl)cyclopentenes by a three-step sequence of ozonolysis, reduction, and acetylation. Rhizopus delemar lipase (RDL)-catalyzed asymmetric hydrolysis of meso-3,5-bis(acetoxymethyl)cyclopentenes afforded the monoalcohols of high enantiomeric purities (> 95% ee) in good yields (64-95%). The obtained monoalcohols 11 and 14 could be applied for the synthesis of antiviral carbocyclic nucleosides (-)-carbovir and (-)-BCA.

Synthesis and anti-HIV activity of 9-[e-4,t-5-bis(hydroxymethyl)cyclopent- 2-en-r-1-yl]-9H-adenine

The synthesis and in vitro anti-HIV activity of two new racemic nucleoside analogues are described; namely, 9-[c-4,t-5-bis(hydroxymethyl)cyclopent-2-en- r-1-yl]-9H-adenine (12) and its guanine analogue 18. While the latter (18) showed no activity, the therapeutic index of the former (12) was 200 and comparable to that (400) of carbovir. One enantiomer of 12 may be viewed as an analogue of carbocyclic oxetanocin and the other as an analogue of carbovir. Hence, these results indicate that one or both of the individual enantiomers of 12 could serve as candidates or lead compounds for the development of anti-AIDS agents.

A NOVEL AND EFFICIENT SYNTHESIS OF 9-(c-4,t-5-BISHYDROXYMETHYLCYCLOPENT-2-EN-r-1-YL)-9H-ADENINE (BCA) HAVING ANTI-HIV ACTIVITY FROM NORBORNADIENE

9-(c-4, t-5-Bishydroxymethylcyclopent-2-en-r-1-yl)-9H-adenine (BCA: 1), a novel carboxylic nucleoside having significant anti-HIV activity, has been synthesized from norbornadiene.

Synthesis of (1R, 4S, 5R)-9-(4,5-bishydroxy-methylcyclopent-2-en-1-yl)-9H-adenine [(-)-BCA] and selective inhibition of human immunodeficiency virus

(1R,4S,5R)-9(4,5-Bishydroxymethylcyclopent-2-en-1-yl)-9H-adenine [(-)-BCA] has been synthesized from (-)-Corey lactone in 11 steps and shown to have potent and selective effects against human immmunodeficiency virus type 1. The result demonstrated that th