138736-93-3

Basic information

• Product Name: (1S,2S)-1,2-Bis(benzoyloxyMethyl)-2,3-diMethyoxy-cyclobutane
• Synonyms: (1S,2S)-1,2-Bis(benzoyloxyMethyl)-2,3-diMethyoxy-cyclobutane
• CAS NO: 138736-93-3
• Molecular Formula: C₂₂H₂₄O₆
• Molecular Weight: 384.42236
• Product Categories: Aromatics;Chiral Reagents;Intermediates;Aromatics, Chiral Reagents, Intermediates
• Mol File: 138736-93-3.mol

Chemical Properties

• Appearance: /
• Solubility: Acetone, Chloroform, Dichloromethane, Ethyl Acetate
• CAS DataBase Reference: (1S,2S)-1,2-Bis(benzoyloxyMethyl)-2,3-diMethyoxy-cyclobutane(CAS DataBase Reference)
• NIST Chemistry Reference: (1S,2S)-1,2-Bis(benzoyloxyMethyl)-2,3-diMethyoxy-cyclobutane(138736-93-3)
• EPA Substance Registry System: (1S,2S)-1,2-Bis(benzoyloxyMethyl)-2,3-diMethyoxy-cyclobutane(138736-93-3)

Safety Data

• Hazardous Substances Data: 138736-93-3(Hazardous Substances Data)

Usage

Chemical Properties

Clear Oil

Upstream product

• 98-88-4 benzoyl chloride 
• 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 

Downstream Products

• 132294-17-8 <(1S)-(1α,2β,3β)>-3-Hydroxy-1,2-cyclobutanedimethanol 1,2-dibenzoate ester 
• 158214-39-2 3(S)-trans-3,4-Bis<(benzoyloxy)methyl>cyclopentanone oxime 
• 138804-29-2 3(S)-trans-3,4-Bis<(benzoyloxy)methyl>cyclopentanone 
• 1576-92-7 (E)-1,4-dibenzoyloxy-2-butene 
• 132294-16-7 (2S-trans)-2,3-bis[(benzoyloxy)methyl]cyclobutanone 

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.

A novel approach toward the synthesis of chiral 2,3-dideoxy nucleosides and their carbocyclic analogues

Photochemical ring-expansion of chiral 2(S),3(R)-bis [(benzoyloxy)methyl]cyclobutanone (3) in the presence of alcohols and acidic N-H functional groups gives anomeric mixtures of acetals and N-amino acetals, respectively, with retention of stereochemistry

An efficient and diastereoselective [2+2] cycloaddition: Convenient and enantioselective route to trans-2',3'-dihydroxymethylcyclobutane nucleoside analogs

An efficient route to (2S-trans)-2,3-bis[(benzoyloxy)methyl]cyclobutanone (3a), a key intermediate in the synthesis of cyclobutane nucleoside analogs, via a novel asymmetric [2+2] cycloaddition, is described.