139893-72-4

Upstream product

• 23600-19-3 methyl 3-O-tosyl-β-D-glucopyranoside 
• 98-59-9 p-toluenesulfonyl chloride 
• 71117-37-8 (2R,4aR,6R,7R,8R,8aS)-6-Methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine-7,8-diol 
• 67-56-1 methanol 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 28538-12-7 methyl 2-O-benzoyl-4,6-O-benzylidene-3-O-p-tolylsulfonyl-α-D-allopyranoside 
• 56253-26-0 methyl 2-O-benzoyl-4,6-O-benzylidene-α-D-allopyranoside 

Downstream Products

• 23600-19-3 methyl 3-O-tosyl-β-D-glucopyranoside 
• 6748-86-3 methyl 4,6-O-benzylidene-3-O-p-tolylsulfonyl-α-D-allopyranoside 
• 120408-72-2 Methyl 2,3-anhydro-4,6-O-(phenylmethylene)-β-D-allopyranoside 

Relevant academic research and scientific papers

Base-promoted rearrangement of sugar epoxides to unsaturated sugars

(Chemical Equation Presented) A simple and efficient method for rearranging 2,3-anhydro carbohydrates to unsaturated sugars has been developed. The exceptionally mild reaction conditions and high stereoselectivity should make this an attractive method for the preparation of unsaturated carbohydrate derivatives.

A glycosylation driven strategy for the synthesis of anomerically pure vinyl sulfone-modified pent-2-enofuranoses and hex-2-enopyranoses

Both α- and β-anomers of vinyl sulfone-modified pent-2-enofuranosides have been synthesized for the first time by taking advantage of the formation of α- and β-methyl glycosides in almost equal ratio only from derivatives of D-xylose. The strategy was equally applicable in the synthesis of α- and β-anomers of vinyl sulfone-modified hex-2-enopyranosides where a D-glucose derivative was selected over a D-allose derivative as the starting material because the former almost exclusively produced the required methyl pyranosides.

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

Stereochemical dependence of the mechanism of deoxygenation, with lithium triethylborohydride, in 4,6-O-benzylidenehexopyranoside p-toluenesulfonates

Lithium triethylborohydride was shown to react with methyl 4,6-O-benzylidene-α-D-hexopyranoside 2- and 3-tosylates, and 2,3-ditosylates, in the manno, allo, and altro configurational series both by O-S fission (O-desulfonylation) and by C-O fission (C-desulfonyloxylation), to produce carbinol and deoxy functions, respectively.The results were compared with those previously obtained with the corresponding gluco and galacto isomers, and the degree of facility of the cleavage reactions was seen to depend on the position of the sulfonic ester groups and the overall configuration of the molecules.The mechanism of reductive desulfonyloxylation also depended on configuration and was demonstrated to involve intermediary epoxide formation or displacement by internal hydride shift as the principal paths; competing elimination and direct nucleophilic displacement were found to occur in the allo series, whereas reduction accompanied by ring contraction has thus far been encountered only in the conformationally less constrained, cis-fused acetal system of the galacto series.Like the borohydride reagent, lithium aluminum hydride was found to react (though much more slowly) with the altro 2,3-ditosylate by the epoxide-mediated mechanism, although the latter hydride is known to desulfonyloxylate the α-D-gluco-isomer by a different, intramolecular reduction mechanism.