Syntheses of spacer-linked neodisaccharides derived from L-Daunosamine

Article abstract of DOI:10.1016/S0040-4039(99)00862-X

The preparation of novel head-to-head spacer-linked bisdaunosamine homodimers 8, 15 and 18 is described. The synthesis is achieved by double glycosylation of monosilylated 1,4-butanediol 9 using silyl glycoside 5 as glycosyl donor. Alternatively, olefin metathesis of allyl glycosides α-11 and particularly of α-12 constitutes a second route toward 8 and its unsaturated derivative 15 while non symmetrical dimer 18 has been obtained by cross metathesis of allyl glycosides 11 and 12.