Syntheses of spacer-linked neodisaccharides derived from L-Daunosamine

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Original languageEnglish
Pages (from-to)4665-4668
Number of pages4
JournalTetrahedron Letters
Volume40
Issue number25
Publication statusPublished - 25 Feb 1999
Externally publishedYes

Abstract

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.

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Syntheses of spacer-linked neodisaccharides derived from L-Daunosamine. / Kirschning, Andreas; Chen, Guang Wu.
In: Tetrahedron Letters, Vol. 40, No. 25, 25.02.1999, p. 4665-4668.

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Kirschning A, Chen GW. Syntheses of spacer-linked neodisaccharides derived from L-Daunosamine. Tetrahedron Letters. 1999 Feb 25;40(25):4665-4668. doi: 10.1016/S0040-4039(99)00862-X
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author = "Andreas Kirschning and Chen, {Guang Wu}",
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T1 - Syntheses of spacer-linked neodisaccharides derived from L-Daunosamine

AU - Kirschning, Andreas

AU - Chen, Guang Wu

N1 - Funding information: Acknowledgement: We thank the Deutsche Forschungsgemeinschaft (SFB 416) as well as the Fonds der Chemischen Industrie for financial support.

PY - 1999/2/25

Y1 - 1999/2/25

N2 - 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.

AB - 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.

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