118353-05-2

Basic information

• Product Name: Carbovir
• Synonyms: carbovir;2-Amino-1,9-dihydro-9-[(1R,4S)-4-(hydroxymethyl)-2-cyclopenten-1-yl]-6H-purin-6-one;2-Amino-9-[(1S)-4α-(hydroxymethyl)-2-cyclopentene-1α-yl]-1,9-dihydro-6H-purine-6-one;2-Amino-9-[4α-(hydroxymethyl)-2-cyclopenten-1α-yl]-1H-purin-6(9H)-one;2-Amino-9-[(1R)-4β-(hydroxymethyl)-2-cyclopenten-1β-yl]-1H-purin-6(9H)-one;2-Amino-9-[(1R)-4β-(hydroxymethyl)-2-cyclopentene-1β-yl]-9H-purine-6-ol;2-Amino-9-[(1R)-4β-hydroxymethyl-2-cyclopentene-1β-yl]-1,9-dihydro-6H-purine-6-one;2-Amino-9-[(1R,4S)-4-(hydroxymethyl)-2-cyclopentenyl]-9H-purine-6-ol
• CAS NO: 118353-05-2
• Molecular Formula: C₁₁H₁₃N₅O₂
• Molecular Weight: 247.25
• Product Categories: Antiviral Agents;Bases & Related Reagents;Inhibitors;Intermediates & Fine Chemicals;Nucleotides;Pharmaceuticals
• Mol File: 118353-05-2.mol
• Article Data: 6

Chemical Properties

• Melting Point: 267-269°C
• Boiling Point: 390.29°C (rough estimate)
• Flash Point: 320.1 °C
• Appearance: /
• Density: 1.2355 (rough estimate)
• Vapor Pressure: 1.62E-15mmHg at 25°C
• Refractive Index: 1.7000 (estimate)
• Storage Temp.: -20?C Freezer
• Solubility: DMSO, Methanol
• Water Solubility: 1.24g/L(25 oC)
• CAS DataBase Reference: Carbovir(CAS DataBase Reference)
• NIST Chemistry Reference: Carbovir(118353-05-2)
• EPA Substance Registry System: Carbovir(118353-05-2)

Safety Data

• Hazardous Substances Data: 118353-05-2(Hazardous Substances Data)

Usage

Chemical Properties

Off-White Solid

Uses

Different sources of media describe the Uses of 118353-05-2 differently. You can refer to the following data:
1. A nucleoside/nucleotide reverse transcriptase inhibitor (NRTI)
2. A nucleoside/nucleotide reverse transcriptase inhibitor (NRTI) caused mitochondrial toxicity in human hepatoma carcinoma cell.

InChI:InChI=1/C11H13N5O2/c12-11-14-9-8(10(18)15-11)13-5-16(9)7-2-1-6(3-7)4-17/h1-2,5-7,17H,3-4H2,(H3,12,14,15,18)

Upstream product

• 140139-15-7 5-(dimethylthexylsilyloxymethyl)cyclopentanone 
• 144363-98-4 cis-5-dimethylthexylsilyloxymethyl-2-cyclopentenol 
• 141192-83-8 6-[2-(trimethylsilyl)ethoxy]-9H-purin-2-amine 
• 144363-96-2 5-dimethylthexylsilyloxymethyl-1-trimethylsilyloxycyclopentene 
• 141192-84-9 cis-1-acetoxy-5-dimethylthexylsilyloxymethyl-2-cyclopentene 
• 144363-97-3 5-dimethylthexylsilyloxymethyl-2-cyclopentenone 
• 152338-04-0 tert-butyldiphenylsilyl (cyclopent-3-enyl)methyl ether 
• 10310-21-1 2-Amino-6-chloropurin 
• 25125-21-7 4-(hydroxymethyl)cyclopentene 
• 49805-30-3 2-azabicyclo[2.2.1.]hept-5-en-3-one 
• 542-92-7 cyclopenta-1,3-diene 
• 109000-07-9 2-(p-tolylsulfonyl)-2-azabicyclo<2.2.1>hept-5-en-3-one 
• 124575-13-9 cis-4-p-toluenesulfonylaminocyclopent-2-enylmethanol 
• 141192-85-0 cis-2-amino-9-<4-(dimethylthexylsilyloxymethyl)-2-cyclopentenyl>-6-(2-trimethylsilylethoxy)purine 

Downstream Products

• 73-40-5 guanine 

Relevant articles and documents

Synthesis of cyclopentenyl carbanucleosides via palladium(0) catalysed reactions

Methyl 4-acetoxycyclopent-2-enylmethylcarboxylate (2) and the corresponding carbonate 3 have been treated with sodium salts and aluminum amides of pyrimidines, purines and methyl 1H-1,2,4-triazole-3-carboxylate with a catalyst formed from bis(dibenzylideneacetone)palladium(0) and triisopropyl phosphite to give the corresponding carbanucleosides in good to excellent yields. This method was also applied for a synthesis of carbovir (31).

New efficient method for the synthesis of the antiviral agent carbovir

An efficient synthesis of (±)-carbovir 1 and simple des(hydroxymethyl) analogues, e.g., 5, is reported which uses a new approach for attaching nucleoside bases to cycloalkene systems.

Pd(0)-catalyzed allylic alkylation in the synthesis of (±)carbovir

Racemic carbovir 1 has been synthesized in 6 steps from the cyclopentanone 8 with a Pd(0)-catalyzed allylation as a key reaction.