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Trimethylsilyl Triflate - Catalysid Acetal Formation Between Silylated Hexopyranosides and Methyl Pyruvate 1

1989; Taylor & Francis; Volume: 8; Issue: 4 Linguagem: Inglês

10.1080/07328308908048022

1532-2327

András Lipták, Lajos Szabó,

Microbial Metabolites in Food Biotechnology

Abstract Trimethylsilyl ethers of 2,3-di-O-substituted glycopyranosides or their thioglycopyranoside analogues were reacted with methyl pyruvate in the presence of trimethylsilyl triflate to give pyruvylated hexo-pyranosides in yields of 60–75%, and the ratio of the diastereoisomers was found to be ca. 1:1. The reaction can also be applied for cellobioside derivatives, providing suitable building blocks for the preparation of pyruvate-containing oligosaccharides.