117641-39-1

Basic information

• Product Name: (1S,2R,3S,5R)-2-(Benzyloxymethyl)-6-oxabicyclo[3.1.0]hexan-3-ol
• Synonyms: (1S,2R,3S,5R)-2-(Benzyloxymethyl)-6-oxabicyclo[3.1.0]hexan-3-ol;[1s-(1α,2α, 3β,5α)]-2-[(phenmethoxy)-methyl]-6-oxabicyclo[3,1,0]hexan-3-ol;Entecavir interMediate 2;Entecavir-2;Entecavir E2;(1S,2R,3S,5R)-2-(Benzyloxymethyl)-6-oxabicyclo[3.1.0]hexan-3-o
• CAS NO: 117641-39-1
• Molecular Formula: C₁₃H₁₆O₃
• Molecular Weight: 220.26
• Mol File: 117641-39-1.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 363.129 °C at 760 mmHg
• Flash Point: 173.415 °C
• Appearance: /
• Density: 1.222
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.579
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 14.36±0.40(Predicted)
• CAS DataBase Reference: (1S,2R,3S,5R)-2-(Benzyloxymethyl)-6-oxabicyclo[3.1.0]hexan-3-ol(CAS DataBase Reference)
• NIST Chemistry Reference: (1S,2R,3S,5R)-2-(Benzyloxymethyl)-6-oxabicyclo[3.1.0]hexan-3-ol(117641-39-1)
• EPA Substance Registry System: (1S,2R,3S,5R)-2-(Benzyloxymethyl)-6-oxabicyclo[3.1.0]hexan-3-ol(117641-39-1)

Safety Data

• Hazardous Substances Data: 117641-39-1(Hazardous Substances Data)

Usage

Uses

(1S,2R,3S,5R)-2-[(Phenylmethoxy)methyl]-6-oxabicyclo[3.1.0]hexan-3-ol, is an impurity of Entecavir (E558900), an oral antiviral drug used in the treatment of hepatitis B infection. A guanine analogue that inhhibits all three steps in the viral replication process.

InChI:InChI=1/C13H16O3/c14-11-6-12-13(16-12)10(11)8-15-7-9-4-2-1-3-5-9/h1-5,10-14H,6-8H2/t10-,11+,12-,13+/m1/s1

Upstream product

• 110567-21-0 (1S,2R)-2-(benzyloxymethyl)-1-hydroxy-3-cyclopentene 
• 668996-19-8 (1S,5R)-5-Benzyloxymethyl-cyclopent-2-enol 
• 542-92-7 cyclopenta-1,3-diene 
• 4984-82-1 sodium cyclopentadienylide 
• 39939-07-6 5-(benzyloxymethyl)cyclopentadiene 
• 3587-60-8 Benzyloxymethyl chloride 
• 668996-17-6 (1R,4S,5S)-5-((benzyloxy)methyl)-4-((4-methoxybenzyl)oxy)cyclopent-2-enol 
• 133299-26-0 (1S,2R,3S,5R)-2-benzyloxymethyl-3-(4-methoxybenzyloxy)-6-oxabicyclo<3.1.0>hexane 

Downstream Products

• 668996-22-3 (1S,2S,5R)-2-Benzyloxymethyl-6-oxa-bicyclo[3.1.0]hexane 
• 668996-14-3 (1S,2S,5R)-2-Benzyloxymethyl-6-oxa-bicyclo[3.1.0]hexan-3-one 
• 668996-12-1 ((1S,2S,3S,5R)-2-Benzyloxymethyl-6-oxa-bicyclo[3.1.0]hex-3-yloxy)-tert-butyl-dimethyl-silane 
• 110567-21-0 (1S,2R)-2-(benzyloxymethyl)-1-hydroxy-3-cyclopentene 
• 668996-31-4 (1R,3S,5R)-3-Benzyloxymethyl-6-oxa-bicyclo[3.1.0]hexan-2-one 
• 668996-24-5 (1α,2β,3α,5α)-3-[(Phenylmethoxy)methyl]-6-oxabicyclo[3.1.0]hexan-2-ol 
• 668996-25-6 (1S,3R,5R)-3-Benzyloxymethyl-2-methylene-6-oxa-bicyclo[3.1.0]hexane 
• 668996-13-2 (1R,4S)-3-[(benzyloxy)methyl]-4-{[tert-butyl(dimethyl)silyl]-oxy}cyclopent-2-en-1-ol 
• 668996-17-6 (1R,4S,5S)-5-((benzyloxy)methyl)-4-((4-methoxybenzyl)oxy)cyclopent-2-enol 
• 668996-26-7 2-benzyloxymethyl-4-(tert-butyl-diphenyl-silanyloxy)-cyclopent-2-enone 
• 668996-15-4 (1S,4R)-2-Benzyloxymethyl-4-(tert-butyl-diphenyl-silanyloxy)-cyclopent-2-enol 
• 114071-49-7 1-(3',5'-di-O-benzyl-2'-deoxy-6'-hydroxy-6'-carba-β-D-ribofuranosyl)thymine 
• 114884-15-0 1-((1R,3S,4R)-3-hydroxy-4-(hydroxymethyl)cyclopentyl)-5-methylpyrimidine-2,4(1H,3H)-dione 
• 648414-58-8 1-(3',5'-di-O-benzyl-2'-deoxy-6'-carba-β-D-ribofuranosyl)thymine 

Relevant articles and documents

A New Route for the Synthesis of Entecavir

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Novel 3′-deoxy analogs of the anti-HBV agent entecavir: Synthesis of enantiomers from a single chiral epoxide

A synthesis of novel 3′-deoxy analogs of the anti-HBV agent entecavir (BMS-200475) was devised using regioselective ring opening of suitable cyclopentene epoxides as the key step. This versatile approach afforded access to an enantiomeric pair of carbocyclic nucleosides from a single chiral intermediate.

Enantioselective synthesis of optically active carbocyclic sugars

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