期刊
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
卷 2012, 期 16, 页码 3122-3131出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201200089
关键词
Carbohydrates; Glycosylation; Glycosyl donors; Regioselectivity
资金
- Ministerio de Ciencia e Innovacion (MICINN) [CTQ2009-10343]
- Comunidad de Madrid [S2009/PPQ-1752]
- National Science Foundation (USA) [CHE 0717702]
Mannopyranose-derived methyl 1,2-orthoacetates (R = Me) and -benzoates (R = Ph) can function as glycosyl donors upon BF3 center dot Et2O activation in CH2Cl2 in glycosylation reactions with monosaccharide acceptors to afford disaccharides in good yields. In the process, glycosylation is preferred to acid-catalyzed rearrangement leading to methyl mannopyranosides. Methyl 1,2-orthoesters can be also used in regioselective glycosylation protocols with monosaccharide diols, in which they display good regioselectivity.
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