124662-92-6

Basic information

• Product Name: Methyl 4,6-O-benzylidene-α-D-galactopyranoside 2-(phenylsulfate)
• CAS NO: 124662-92-6
• Molecular Weight: 438.455
• Mol File: 124662-92-6.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: Methyl 4,6-O-benzylidene-α-D-galactopyranoside 2-(phenylsulfate)(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl 4,6-O-benzylidene-α-D-galactopyranoside 2-(phenylsulfate)(124662-92-6)
• EPA Substance Registry System: Methyl 4,6-O-benzylidene-α-D-galactopyranoside 2-(phenylsulfate)(124662-92-6)

Safety Data

• Hazardous Substances Data: 124662-92-6(Hazardous Substances Data)

Upstream product

• 4288-93-1 methyl 4,6-O-benzylidene-α-D-galactopyranoside 
• 16475-29-9 phenylchlorosulfate 
• 3162-96-7 methyl 4,6-O-benzylidene-α-D-glucopyranoside 

Downstream Products

• 124663-00-9 Acetic acid (4aR,6S,7R,8S,8aS)-6-methoxy-7-phenoxysulfonyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester 
• 124663-00-9 Acetic acid (4aR,6S,7R,8S,8aR)-6-methoxy-7-phenoxysulfonyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester 

Relevant articles and documents

REACTIONS OF PHENYL CHLOROSULFATE AT OH-2 AND OH-3 OF ALDOHEXOPYRANOSE DERIVATIVES. COMPETING SUBSTITUTION AND DISPLACEMENT REACTIONS

Reactions of phenyl chlorosulfate-sodium hydride with methyl 4,6-O-benzylidenealdohexopyranosides are characterized by a variety of nucleophilic substitution and displacement processes involving OH-2 and -3 of the glycosides.Depending on such factors as the relative rates of substitution of these two hydroxyl groups and their configurations, as well as temperature and stoichiometry, the products may be mono- or di-phenylsulfates (or both), 2,3-cyclic sulfates, or 2,3-oxiranes.For example, in the reaction of methyl 4,6-O-benzylidene-α-D-glucopyranoside with two equivalents of phenyl chlorosulfate at +25deg, the products were the 2,3-disulfate (10percent), 2,3-cyclic sulfate (77percent), and 2,3-allo epoxide (4percent), whereas, at -25deg, by far the major product was the 2-phenylsulfate (79percent).Intramolecular displacement was so readily facilitated in the reaction of methyl 4,6-O-benzylidene-α-D-altropyranoside that the only products obtained were the 2,3-anhydro-manno- (major) and -allo-pyranosides.Conformations of the 2,3-cyclic sulfates are considered on the basis of their n.m.r. characteristics.