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Synlett 1998; 1998(5): 487-488
DOI: 10.1055/s-1998-1706
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Simplifying Oligosaccharide Synthesis: Boronate Diesters as Cleavable Protecting Groups

G. G. Cross* , D. M. Whitfield
  • *National Research Council, Institute for Biological Sciences, Ottawa, Ontario, Canada K1A 0R6; Fax (613)952-9092; E-mail: dennis.whitfield@nrc.ca
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Publication History

Publication Date:
31 December 2000 (online)

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Phenyl boronate diester was used as a cleavable protecting group on thioglycoside donors. Procedures to glycosylate the polymer linker combination MPEG-DOXOH were developed. The boronate diester was readily removed and the resulting diols regioselectively glycosylated using silver triflate promotion of a trichloroacetimidate donor. Subsequent protecting group manipulations and cleavage from the polymer yielded peracetylated disaccharides in good yields. The whole sequence requires only one chromatography and is therefore much simpler than traditional procedures.

polymer-supported - oligosaccharides - boronate diesters - silver triflate - ethylenediamine