84207-38-5

Upstream product

• 98-59-9 p-toluenesulfonyl chloride 
• 612-05-5 methyl-β-D-xylopyranoside 
• 118203-99-9 methyl 2,3-O-isopropylidene-β-D-xylopyranoside 
• 2500-82-5 Toluene-4-sulfonic acid (3aR,4R,7R,7aR)-4-methoxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl ester 

Downstream Products

• 137600-24-9 methyl 3-deoxy-α-L-threo-pentopyranoside di-O-benzoate 
• 83158-32-1 methyl 2,3-di-O-benzoyl-4-O-p-toluenesulfonyl-β-D-xylopyranoside 
• 137600-22-7 methyl 2,3-di-O-benzoyl-4-deoxy-β-L-threo-pentopyranoside 
• 6638-76-2 1-O-methyl-2,3,4-O-tri-benzoyl-β-D-xylopyranoside 
• 14621-31-9 methyl 2,3-anhydro-α-D-lyxopyranoside 
• 137600-21-6 methyl 3,4-anhydro-α-L-arabinopyranoside 
• 1073186-64-7 methyl O²-benzoyl-O⁴-p-toluenesulfonyl-β-D-xyloside 

Relevant academic research and scientific papers

Efficient synthesis of 4-amino-4-deoxy-L-arabinose and spacer-equipped 4-amino-4-deoxy-L-arabinopyranosides by transglycosylation reactions

Methyl 4-azido-4-deoxy-l-arabinopyranoside has been synthesized in five steps starting from methyl-d-xylopyranoside in a multigram scale without chromatographic purification in 78% overall yield. The transformation relied on selective tosylation/nosylatio

Regioselective protection of sugars catalyzed by dimethyltin dichloride

(Chemical Equation Presented) The first catalytic process for protection of hydroxyl groups in sugars has been developed. Highly regioselective protection was accomplished along with high chemical yield. The regioselectivity of the benzoylation was realiz

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