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Synthesis 1992; 1992(10): 1013-1017
DOI: 10.1055/s-1992-26291
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Convenient Synthesis of 4,6-O-Pyruvate Acetal Containing Glycosides via Tetraisopropyldisiloxanediyl Protected Sugars

Thomas Ziegler* , Elisabeth Eckhardt, Karin Neumann, Veronique Birault
  • *Institut für Organische Chemie and Isotopenforschung, Universität Stuttgart, Pfaffenwaldring 55, D-7000 Stuttgart 80, Germany
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Publication Date:
17 September 2002 (online)

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Treatment of alkyl D-glycopyranosides and alkyl or phenyl 1-thio-ß-D-glycopyranosides 1 with 1,3-dichloro-1,1,3,3-tetraisopropyldisiloxane gave the corresponding 4,6-O-(1,1,3,3-tetraisopro-pyldisiloxane-1,3-diyl) protected glycosides 2 which were subsequently benzoylated with benzoyl bromide to give the fully blocked glycosides 3. Reaction of the latter with methyl pyruvate and a catalytic amount of trimethylsilyl trifluoromethanesulfonate gave alkyl and phenyl 4,6-O-[1-(methoxycarbonyl)ethylidene]glycopyranosides 4 with high diastereoselectivity.

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