Stereoselective O-glycosylation reactions using glycosyl donors with diphenylphosphinate and propane-1,3-diyl phosphate leaving groups
2001; Elsevier BV; Volume: 12; Issue: 9 Linguagem: Inglês
10.1016/s0957-4166(01)00227-0
ISSN1362-511X
AutoresHariprasad Vankayalapati, Gurdial Singh, Isabelle Tranoy,
Tópico(s)Enzyme Catalysis and Immobilization
ResumoGlycosyl donors having a diphenylphosphinate and a propane-1,3-diyl phosphate leaving group were easily prepared by the addition of the anomeric hydroxyl group of 2,3,4,6-tetra-O-benzyl-α,β-d-glucopyranose to diphenylphosphinic and propane-1,3-diyldioxyphosphoryl chlorides. These glycosyl donors were selectively glycosylated with a number of primary and secondary oxygen nucleophiles in the presence of trimethylsilyl triflate (TMSOTf). The use of 1,3-diyl phosphate resulted in the stereoselective formation of β-O-linked glycosides.
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