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Title
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Stannylene-mediated regioselective 6-O-glycosylation of unprotected phenyl 1-thioglycopyranosides
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Author
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Abstract
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| A straightforward procedure is described for the synthesis of (1[RIGHTWARDS ARROW]6)-linked saccharides by regioselective glycosylation of unprotected glycosyl acceptors. Phenyl 1-thioglycopyranosides derived from D-glucose, D-galactose and D-mannose were treated with dibutyltin oxide to introduce a stannylene acetal, and then subjected to selective glycosylation at the 6-position with the KoenigsKnorr protocol. Peracylated glycosyl bromides of D-glucose, D-galactose, D-mannose and D-glucosamine were employed as the donors to give the corresponding (1[RIGHTWARDS ARROW]6)-linked disaccharides in moderate to good yields. The best results were obtained with glycosyl donors and acceptors derived from D-glucose and D-galactose. Fully acylated disaccharide thioglycosides could also serve as glycosyl donors for the regioselective coupling. Brominolysis and subsequent KoenigsKnorr coupling with the stannylene acetal of phenyl 1-thio-β-D-glucopyranoside gave rise to the corresponding (1[RIGHTWARDS ARROW]6)-linked trisaccharides in moderate yields. |
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Language
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English
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Source (journal)
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European journal of organic chemistry. - Weinheim, 1998, currens
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Publication
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Weinheim
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2013
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ISSN
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1434-193X
[print]
1099-0690
[online]
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DOI
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10.1002/EJOC.201300026
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Volume/pages
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13
(2013)
, p. 2683-2691
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ISI
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000318043000022
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Full text (Publisher's DOI)
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Full text (publisher's version - intranet only)
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