124040-31-9

Basic information

• Product Name: methyl 2,3-di-O-benzyl-β-D-glucopyranoside 6-(phenylsulfate)
• Synonyms: methyl 2,3-di-O-benzyl-β-D-glucopyranoside 6-(phenylsulfate)
• CAS NO: 124040-31-9
• Molecular Weight: 530.596
• Mol File: 124040-31-9.mol

Chemical Properties

• CAS DataBase Reference: methyl 2,3-di-O-benzyl-β-D-glucopyranoside 6-(phenylsulfate)(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 2,3-di-O-benzyl-β-D-glucopyranoside 6-(phenylsulfate)(124040-31-9)
• EPA Substance Registry System: methyl 2,3-di-O-benzyl-β-D-glucopyranoside 6-(phenylsulfate)(124040-31-9)

Safety Data

• Hazardous Substances Data: 124040-31-9(Hazardous Substances Data)

Upstream product

• 16475-29-9 phenylchlorosulfate 
• 6988-40-5 methyl 2,3-di-O-benzyl-β-D-glucopyranoside 

Downstream Products

• 124040-32-0 Acetic acid (2R,3R,4S,5R,6R)-4,5-bis-benzyloxy-6-methoxy-2-phenoxysulfonyloxymethyl-tetrahydro-pyran-3-yl ester 
• 124040-36-4 Acetic acid (2S,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-((2R,3R,4S,5R,6R)-4,5-bis-benzyloxy-6-methoxy-2-phenoxysulfonyloxymethyl-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-3-yl ester 

Relevant articles and documents

REACTIONS OF PHENYL CHLOROSULFATE AT OH-1, -4, AND -6 OF ALDOHEXOPYRANOSE DERIVATIVES. FORMATION OF 1,2-OXAZOLINE AND 4,6-CYCLIC SULFATE RINGS

In the reaction of phenyl chlorosulfate-sodium hydride with compounds having both OH-4 and OH-6 free, as in methyl 2,3-di-O-benzylaldohexopyranosides, either regioselective substitution of the primary hydroxyl group occurs, or a 4,6-cyclic sulfate is formed, depending on the experimental conditions.The addition of a 6-(phenylsulfate) substituent to the di-O-benzylglycosides appears to cause little or no interference with disaccharide synthesis at the nearby O-4 atom.Conformations of both cis- and trans-fused types of 4,6-cyclic sulfates are discussed.At an unsubstituted anomeric center, the course of reaction by phenyl chlorosulfate is determined by neighboring-group participation possibilities, and the strong leavinggroup affinity of a phenylsulfate substituent.This is demonstrated by a 60percent conversion of 2-acetamido-4,6-O-benzylidene-2-deoxy-D-glucopyranose into the corresponding 1,2-oxazoline derivative, in contrast to the formation of a mixture of anomeric glycosides and (11) disaccharide when the O-2 substituent is benzyl.