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Review | Special issue | Vol 76, No. 2, 2008, pp.883-908
Published online, 29th May, 2008
DOI: 10.3987/REV-08-SR(N)4
DTBS Effect: The Unique Sterically Driven Director for α-Galactosylation

Akihiro Imamura, Hiromune Ando, Hideharu Ishida, and Makoto Kiso*

*Gifu University, 1-1 Yanagido, Gifu-shi, Gifu 501-1193, Japan

Abstract

This review outlines the chemistry of 1,2-cis glycosylations and discusses the state-of-the-art methods, highlighting the DTBS(di-tert-butylsilylene)-directed α-galactosylation that was recently developed by our group. The key feature of our unique methodology includes extremely simple procedure, namely, the introduction of cyclic DTBS protecting group into 4- and 6-OH at galacto-type glycosyl donor. The power of the methodology was demonstrated by the syntheses of biologically relevant glycans including mucin-type glycosyl amino acids [α-O-GalNAc-Ser/Thr], α-galactosyl ceramides, globo-series glycolipids.