Synthesis and glycosylating properties of ketopyranosyl donors

The preparation of heptulopyranosyl donors 13–15, 28, 29 and 3-octulopyranosyl donors 34, 35, having a non-participating group at C-3 or C-4, respectively, is described. Glycosylations of various acceptors with these donors gave exclusively α-linked ketosides. On the other hand, condensation of 3-O-...

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Bibliographic Details
Published in:Tetrahedron 1995-05, Vol.51 (19), p.5657-5670
Main Authors: Heskamp, B.M., Veeneman, G.H., van der Marel, G.A., van Boeckel, C.A.A., van Boom, J.H.
Format: Article
Language:English
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Summary:The preparation of heptulopyranosyl donors 13–15, 28, 29 and 3-octulopyranosyl donors 34, 35, having a non-participating group at C-3 or C-4, respectively, is described. Glycosylations of various acceptors with these donors gave exclusively α-linked ketosides. On the other hand, condensation of 3-O-benzoyl heptulopyranosyl donor 19 with an acceptor furnished an anomeric mixture of ketodisaccharides. D- Galacto- and L- fuco-hetulopyranosyllas well as L- fuco-3-octulopyranosyl donors 1–4 were prepared from the corresponding perbenzylated 1,5-lactones and employed in the synthesis of ketodisaccharides.
ISSN:0040-4020
1464-5416
DOI:10.1016/0040-4020(95)00225-W