Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2008, Issue 25, Pages 4250-4263Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.200800249
Keywords
1,2-cis-glycosides; intramolecular aglycon delivery (IAD); stereoselective synthesis; glycosylation; oligosaccharides
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Funding
- Ecomolecular Science and Chemical Biology programs in RIKEN
- Ministry of Education, Culture, Sports, Science, and Technology [18710196]
- Grants-in-Aid for Scientific Research [18710196] Funding Source: KAKEN
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A methodology directed towards the stereoselective construction of 1,2-cis-glycosides through naphthylmethyl (NAP) ether mediated intramolecular aglycon derivery (IAD) has been developed. Stereospecific constructions of various 1,2-cis linkages, as in beta-mannopyrano-, beta-arabinofurano-, and alpha-glucopyranosides, were achieved through NAP-IAD. This methodology was successfully applied to the synthesis of Glc alpha(1 -> 2)-Glc alpha(1 -> 3)-Glc alpha(1 -> 3)Man (Glc(3)Man(1)), the non-reducing terminal structure of the tetradecasaccharide Glc(3)Man(9)GlcNAc(2), a common precursor of all N-linked glycans. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008).
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