132294-16-7

Basic information

• Product Name: (2S,3S)-2,3-BIS(BENZOYLOXYMETHYL)CYCLOBUTANONE
• Synonyms: (2S,3S)-2,3-BIS(BENZOYLOXYMETHYL)CYCLOBUTANONE;(2S-trans)-2,3-Bis[(benzoyloxy)Methyl]cyclobutanone
• CAS NO: 132294-16-7
• Molecular Formula: C₂₀H₁₈O₅
• Molecular Weight: 338.35
• Product Categories: Aromatics;Chiral Reagents;Intermediates
• Mol File: 132294-16-7.mol
• Article Data: 13

Chemical Properties

• Melting Point: 97-98 °C
• Boiling Point: 486.5±10.0 °C(Predicted)
• Appearance: /
• Density: 1.234±0.06 g/cm3(Predicted)
• Solubility: Chloroform, Dichloromethane, Ethyl Acetate
• CAS DataBase Reference: (2S,3S)-2,3-BIS(BENZOYLOXYMETHYL)CYCLOBUTANONE(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,3S)-2,3-BIS(BENZOYLOXYMETHYL)CYCLOBUTANONE(132294-16-7)
• EPA Substance Registry System: (2S,3S)-2,3-BIS(BENZOYLOXYMETHYL)CYCLOBUTANONE(132294-16-7)

Safety Data

• Hazardous Substances Data: 132294-16-7(Hazardous Substances Data)

Usage

Uses

Intermediate in the preparation of carbocyclic nucleoside derivatives.

Upstream product

• 132294-15-6 (1S-trans)-3,3-diethoxy-1,2-cyclobutanedimethanol dibenzoate ester 
• 132178-71-3 trans-3,3-diethoxy-1,2-cyclobutanedicarboxylic acid 
• 127696-10-0 trans-3,3-diethoxy-1,2-cyclobutanedicarboxylic acid diethyl ester 
• 132178-72-4 <1S-<1α(S^*),2β(S^*)>>-3,3-diethoxy-N,N'-bis-(2-hydroxy-1-phenylethyl)-1,2-cyclobutanedicarboxamide 
• 104-15-4 toluene-4-sulfonic acid 
• 126261-70-9 (+/-)-trans-1,2-bis-(3,3-diethoxycyclobutylen)methanol 
• 15210-38-5 (trans)-3,3-diethoxy-1,2-cyclobutanedicarboxylic acid,diethyl ester 
• 124770-79-2 C₂₄H₂₈O₆ 
• 124770-79-2 C₂₄H₂₈O₆ 
• 98-88-4 benzoyl chloride 
• 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 
• 138736-91-1 (1S,2R)-3,3-Dimethoxy-cyclobutane-1,2-dicarboxylic acid bis-((1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl) ester 

Downstream Products

• 1576-92-7 (E)-1,4-dibenzoyloxy-2-butene 
• 69827-96-9 Methyl 5-O-benzoyl-3-C<(benzoyloxy)methyl>-2,3-dideoxy-β-D-erythro-pentofuranose 
• 132294-17-8 <(1S)-(1α,2β,3β)>-3-Hydroxy-1,2-cyclobutanedimethanol 1,2-dibenzoate ester 
• 127759-89-1 lobucavir 
• 132294-18-9 <1S-(1α,2β,3β)>-3-<<(4-methylphenyl)sulfonyl>oxy>-1,2-cyclobutanedimethanol dibenzoate ester 
• 132294-20-3 (1'S,2'S,3'R)-9-[2',3'-bis(benzoyloxymethyl)cyclobutyl]adenine 
• 132294-19-0 <1S-(1α,2β,3α)>-3-<2-amino-6-(phenylmethoxy)-9H-purin-9-yl>-1,2-cyclobutanedimethanol 1,2-dibenzoate ester 
• 126261-73-2 C₂₀H₂₀O₅ 
• 124794-61-2 C₂₅H₃₃ClN₄O₄ 
• 124794-61-2 C₂₅H₃₃ClN₄O₄ 
• 124770-84-9 C₂₅H₃₅N₅O₄ 
• 124770-84-9 C₂₅H₃₅N₅O₄ 
• 124770-82-7 (1,2-trans)-1-amino-2,3-bis(cyclohexylcarbonyloxymethyl)cyclobutane 

Relevant articles and documents

A Stereocontrolled Synthesis of a Phosphorothioate Cyclic Dinucleotide-Based STING Agonist

We describe a stereodefined synthesis of the newly identified non-natural phosphorothioate cyclic dinucleotide (CDN) STING agonist, BMT-390025. The new route avoids the low-yielding racemic approach using P(III)-based reagents, and the stereospecific assembly of the phosphorothioate linkages are forged via the recently invented P(V)-based platform of the so-called PSI (Ψ) reagent system. This P(V) approach allows for the complete control of chirality of the P-based linkages and enabled conclusive evidence of the absolute configuration. The new approach offers robust procedures for preparing the stereodefined CDN in eight steps starting from advanced nucelosides, with late-stage direct drop isolations and telescoped steps enabling an efficient scale-up that proceeded in an overall 15% yield to produce multigram amounts of the CDN.

CYCLIC DINUCLEOTIDES AS ANTICANCER AGENTS

The present invention is directed to compounds of the formulae I, II and III as shown below wherein all substituents are defined herein, as well as pharmaceutically acceptable compositions comprising compounds of the invention and methods of using said compositions in the treatment of various disorders.

Process for the preparation of an antiviral agent

(1R,trans) Diprotected 3-methylene-1,2-cyclopropanedimethanol is oxidized to an optically active diol STR1 which is then cyclized to an orthoester STR2 This orthoester is then treated with a Lewis acid catalyst to give the cyclobutanone STR3 which is useful as an intermediate in the preparation of the antiviral agent ?1R-(1α,2β,3α)!-2-amino-9-?2,3-bis(hydroxymethyl)cyclobutyl!-1,9-dihydro-6H-purin-6-one.