Abstract
AbstractThe effectiveness in terms of yield and stereoselectivity of (phenylsulfinyl)piperidine (BSP) 1b/ trifluoromethanesulfonic anhydride (Tf2O) and diphenyl sulfoxide (DPS) 1c/Tf2O‐mediated glycosidations of 2‐azido‐3‐O‐benzyl‐4,6‐O‐benzylidene‐2‐deoxy‐D‐thiomannosides 2a/b is described. Application of the BSP/Tf2O activator led to productive condensations using p‐methoxyphenyl 2‐azido‐3‐O‐benzyl‐4,6‐O‐benzylidene‐2‐deoxy‐D‐thiomannoside (2b) as a donor, while the more powerful DPS/Tf2O combination gave similar results using both p‐methoxyphenyl and phenyl 2‐azido‐3‐O‐benzyl‐4,6‐O‐benzylidene‐2‐deoxy‐D‐thiomannosides 2a/b. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)
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