14262-63-6

Upstream product

• 98-59-9 p-toluenesulfonyl chloride 
• 91-09-8 methyl-α-D-xylopyranoside 

Downstream Products

• 83158-23-0 methyl 2,3-di-O-benzoyl-4-O-p-toluenesulfonyl-α-D-xylopyranoside 
• 137600-23-8 methyl 4-deoxy-β-L-threo-pentopyranoside di-O-benzoate 
• 10225-78-2 methyl 2,3,4-tri-O-benzoyl-α-D-xylopyranoside 
• 13143-95-8 methyl 4-azido-2,3-di-O-benzoyl-4-deoxy-β-L-arabinopyranoside 

Relevant academic research and scientific papers

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.

Selective monosulfonylation of internal 1,2-diols catalyzed by di-n- butyltin oxide

The reaction of internal 1,2-diols with catalytic n-Bu2SnO, p-TsCl (1.05 equiv.) and Et3N (1.1 equiv.) led to selective monotosylation. In the case of cyclic substrates, the cis-1,2-diol moiety appeared best suited for optimal results, supporting the intermediacy of a five-membered chelate. (C) 2000 Elsevier Science Ltd.

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