Practical synthesis of active O-2-(2-propylsulfinyl)benzyl (OPSB) glycosides via a catalytic and metal free oxidation of latent O-2-(2-propylthiol)benzyl (OPTB) glycosides

Carbohydrate Research
Ying XiaoQian Wan

Abstract

A catalytic and metal free sulfoxidation of O-2-(2-propylthiol)benzyl (OPTB) glycosides to O-2-(2-propylsulfinyl)benzyl (OPSB) glycosides has been developed by introducing NOBF4 as catalyst, oxygen as terminal oxidant and TBAB as additive. Wide variety of OPTB glycosides were efficiently oxidized without observation of over oxidation. The allowance of large scale synthesis, easy operation and purification highlighted its practical application in construction of complex oligosaccharides and glycoconjugates employing interrupted Pummerer reaction mediated glycosylation strategy.

Citations

Feb 28, 2020·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Xiang ZhaoQian Wan

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