460082-42-2

Basic information

• Product Name: phenyl 2-O-benzoyl-3,4-di-O-benzyl-6-O-mesyl-1-thio-β-D-glucopyranoside
• Synonyms: phenyl 2-O-benzoyl-3,4-di-O-benzyl-6-O-mesyl-1-thio-β-D-glucopyranoside
• CAS NO: 460082-42-2
• Molecular Weight: 634.771
• Mol File: 460082-42-2.mol

Chemical Properties

• CAS DataBase Reference: phenyl 2-O-benzoyl-3,4-di-O-benzyl-6-O-mesyl-1-thio-β-D-glucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: phenyl 2-O-benzoyl-3,4-di-O-benzyl-6-O-mesyl-1-thio-β-D-glucopyranoside(460082-42-2)
• EPA Substance Registry System: phenyl 2-O-benzoyl-3,4-di-O-benzyl-6-O-mesyl-1-thio-β-D-glucopyranoside(460082-42-2)

Safety Data

• Hazardous Substances Data: 460082-42-2(Hazardous Substances Data)

Upstream product

• 460082-41-1 phenyl 2-O-benzoyl-3-O-benzyl-4,6-O-benzylidene-1-thio-β-D-glucopyranoside 
• 98-88-4 benzoyl chloride 
• 128848-51-1 phenyl 3-O-benzyl-4,6-O-benzylidene-1-deoxy-1-thio-β-D-glucopyranoside 
• 124-63-0 methanesulfonyl chloride 
• 221459-61-6 phenyl 2-O-benzoyl-3,4-di-O-benzyl-1-thio-β-D-glucopyranoside 

Downstream Products

• 460082-43-3 phenyl 2-O-benzoyl-3,4-di-O-benzyl-6-deoxy-1-thio-β-D-glucopyranoside 

Relevant articles and documents

Preparation and diastereomeric separation of an (S)- and (R)-1-(methoxycarbonyl)tridec-10-yl glucoside derivative, a precursor for a monosaccharide constituent of resin glycosides.

The 6-O-mesyl derivative of phenyl 1-thio-beta-D-glucopyranoside was prepared from D-glucose as a synthetic equivalent of a 6-deoxy-hexosyl donor. Racemic methyl 11-hydroxytetradecanoate (methyl convolvulinolate) was synthesized by Grignard reaction of propylmagnesium bromide with 10-undecenal followed by hydroboration. Both intermediates were coupled by NIS-TfOH-promoted glycosidation to give a mixture of two diasteromeric glucopyranosides, which were separated on a preparative scale by medium pressure chromatography. One of the products was identified as having the natural (S)-configuration by comparison of its 1H NMR spectrum with an authentic sample prepared from the corresponding chiral hydroxyfatty acid.