132294-17-8

Basic information

• Product Name: (1S,2S,3S)-2,3-Bis(benzoyloxymethyl)cyclobutanol
• Synonyms: (1S,2S,3S)-2,3-Bis(benzoyloxymethyl)cyclobutanol;[1S-(1α,2β,3β)]-3-Hydroxy-1,2-cyclobutanediMethanol 1,2-Dibenzoate
• CAS NO: 132294-17-8
• Molecular Formula: C₂₀H₂₀O₅
• Molecular Weight: 340.3698
• Product Categories: Aromatics;Chiral Reagents;Intermediates
• Mol File: 132294-17-8.mol
• Article Data: 8

Chemical Properties

• Melting Point: 73 °C
• Boiling Point: 487.4±10.0 °C(Predicted)
• Appearance: /
• Density: 1.239±0.06 g/cm3(Predicted)
• Solubility: Chloroform, Ether
• PKA: 14.62±0.60(Predicted)
• CAS DataBase Reference: (1S,2S,3S)-2,3-Bis(benzoyloxymethyl)cyclobutanol(CAS DataBase Reference)
• NIST Chemistry Reference: (1S,2S,3S)-2,3-Bis(benzoyloxymethyl)cyclobutanol(132294-17-8)
• EPA Substance Registry System: (1S,2S,3S)-2,3-Bis(benzoyloxymethyl)cyclobutanol(132294-17-8)

Safety Data

• Hazardous Substances Data: 132294-17-8(Hazardous Substances Data)

Usage

Chemical Properties

White Solid

Uses

Intermediate in the preparation of carbocyclic nucleoside derivatives.

Upstream product

• 124770-80-5 trans-2,3-bis(benzoyloxymethyl)cyclobutanone 
• 124770-79-2 C₂₄H₂₈O₆ 
• 127696-10-0 trans-3,3-diethoxy-1,2-cyclobutanedicarboxylic acid diethyl ester 
• 126261-70-9 (+/-)-trans-1,2-bis-(3,3-diethoxycyclobutylen)methanol 
• 98-88-4 benzoyl chloride 
• 138736-93-3 C₂₂H₂₄O₆ 
• 138736-92-2 (2S,3R)-(+)-bis[hydroxymethyl]-1,1-dimethoxycyclobutane 
• 138736-91-1 (1S,2R)-3,3-Dimethoxy-cyclobutane-1,2-dicarboxylic acid bis-((1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl) ester 
• 1013657-42-5 C₃₇H₄₆O₅ 
• 132178-72-4 <1S-<1α(S^*),2β(S^*)>>-3,3-diethoxy-N,N'-bis-(2-hydroxy-1-phenylethyl)-1,2-cyclobutanedicarboxamide 
• 132294-15-6 (1S-trans)-3,3-diethoxy-1,2-cyclobutanedimethanol dibenzoate ester 
• 132294-14-5 (1S-trans)-3,3-diethoxy-1,2-cyclobutanedimethanol 
• 132178-74-6 C₃₈H₆₀N₄O₈Si₂ 
• 132178-73-5 [1S-[1α(S*),2β(S*)]]-N,N'-Bis[2-[[(1,1-dimethylethyl) dimethylsilyl]oxy]-1-phenylethyl]-3,3-diethoxy-1,2-cyclobutanedicarboxamide 

Downstream Products

• 132294-19-0 <1S-(1α,2β,3α)>-3-<2-amino-6-(phenylmethoxy)-9H-purin-9-yl>-1,2-cyclobutanedimethanol 1,2-dibenzoate ester 
• 132294-20-3 (1'S,2'S,3'R)-9-[2',3'-bis(benzoyloxymethyl)cyclobutyl]adenine 
• 127759-89-1 lobucavir 
• 126261-75-4 C₃₂H₂₉N₅O₅ 
• 126062-18-8 (+/-)-9-<(1β,2α,3β)-2,3-bis(hydroxymethyl)-1-cyclobutyl>guanine 
• 182686-31-3 C₂₁H₂₁NO₄S 
• 182686-30-2 C₂₁H₂₁NO₅ 

Relevant articles and documents

A practical asymmetric synthesis of the antiviral agent lobucavir, BMS-180194

A practical synthesis of the antiviral agent lobucavir, [1R-(1α,2β,3α)]-2-amino-9-[2,3-bis(hydroxymethyl)cyclobutyl]- 6H-purin-6-one (BMS-180194), is described. The key chiral intermediate, [1S-(1α,2β,3α)]-3-hydroxy-1,2-cyclobutanedimethanol, dibenzoate e

CYCLOBUTYL NUCLEOSIDE ANALOGS AS ANTI-VIRALS

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Expedient approach to chiral cyclobutanones: Asymmetric synthesis of cyclobut-G

An efficient one-pot asymmetric synthesis of cyclobutanones from chiral enol ethers is described. The approach is illustrated with alkyl- and functionalized alkyl-substituted enol ethers (nine examples). A new enantioselective synthesis of cyclobut-G (Lobucavir) could thus be achieved.