14187-86-1

Basic information

• Product Name: methyl 2-O-p-toluenesulfonyl-α-D-xylopyranoside
• Synonyms: methyl 2-O-p-toluenesulfonyl-α-D-xylopyranoside
• CAS NO: 14187-86-1
• Molecular Weight: 318.348
• Mol File: 14187-86-1.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: methyl 2-O-p-toluenesulfonyl-α-D-xylopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 2-O-p-toluenesulfonyl-α-D-xylopyranoside(14187-86-1)
• EPA Substance Registry System: methyl 2-O-p-toluenesulfonyl-α-D-xylopyranoside(14187-86-1)

Safety Data

• Hazardous Substances Data: 14187-86-1(Hazardous Substances Data)

Upstream product

• 98-59-9 p-toluenesulfonyl chloride 
• 91-09-8 methyl-α-D-xylopyranoside 
• 50-69-1 D-ribose 
• 53796-89-7 methyl 3,4-O-isopropylidene-2-O-p-tolylsulfonyl-β-D-ribopyranoside 

Downstream Products

• 6638-76-2 1-O-methyl-2,3,4-O-tri-benzoyl-β-D-xylopyranoside 
• 83158-24-1 methyl 3,4-di-O-benzoyl-2-O-tosyl-α-D-xylopyranoside 

Relevant articles and documents

Catalytic regioselective sulfonylation of α-chelatable alcohols: Scope and mechanistic insight

This paper describes a convenient protocol for the regioselective sulfonylation of α-chelatable alcohols. Typically, the reaction of α-heterosubstituted alcohols with 1 equiv of p-TsCl and 1 equiv of Et3N in the presence of 2 mol % of Bu2SnO leads to rapid, regioselective, and exclusive monotosylation. The pKa of the amine was correlated to the reaction rate. A plausible mechanism for this reaction has been proposed on the basis of 119Sn NMR studies.

Regioselective monotosylation of non-protected and partially protected glycosides by the dibutyltin oxide method

Tosylation of non-protected glycopyranosides with p-toluenesulfonyl chloride in the presence of 4-dimethylaminopyridine, after activiation of the glycosides by dibutyltin oxide, gave mono-O-tosylates in good yield. The regioselectivity in this tosylation