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
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 wi...
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Veröffentlicht in: | Carbohydrate research 2018-11, Vol.469, p.10-13 |
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Hauptverfasser: | , , , , , , , |
Format: | Artikel |
Sprache: | eng |
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Zusammenfassung: | 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.
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•Catalytic and metal free oxidation reactions with O2 as terminal oxidant.•Simple manipulation and purification processes.•Wide functional group tolerance and large-scale synthesis. |
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ISSN: | 0008-6215 1873-426X |
DOI: | 10.1016/j.carres.2018.08.014 |