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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.… Click to show full 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.
Journal Title: Carbohydrate research
Year Published: 2018
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