Highly β-Selective and Direct Formation of 2-O-Glycosylated Glucosides by Ring Restriction into Twist-Boat

Three disaccharide donors, ethyl 2-O-(2,3,4-tris-O-tert-butyldimethylsilyl-β-d-xylopyranosyl)-3,4,6-tris-O-tert-butyldimethylsilyl-1-thio-β-d-glucopyranoside, ethyl 2-O-(2,3,4-tris-O-tert-butyldimethylsilyl-α-l-rhamnopyranosyl)-3,4,6-tris-O-tert-butyldimethylsilyl-1-thio-β-d-glucopyranoside, and eth...

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Bibliographic Details
Published in:Organic letters 2007-07, Vol.9 (15), p.2755-2758
Main Authors: Okada, Yasunori, Nagata, Osamu, Taira, Miyoko, Yamada, Hidetoshi
Format: Article
Language:English
Subjects:
Carbohydrate Conformation
Glucosides - chemistry
Glycosylation
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Summary:Three disaccharide donors, ethyl 2-O-(2,3,4-tris-O-tert-butyldimethylsilyl-β-d-xylopyranosyl)-3,4,6-tris-O-tert-butyldimethylsilyl-1-thio-β-d-glucopyranoside, ethyl 2-O-(2,3,4-tris-O-tert-butyldimethylsilyl-α-l-rhamnopyranosyl)-3,4,6-tris-O-tert-butyldimethylsilyl-1-thio-β-d-glucopyranoside, and ethyl 2-O-(2,3,4,6-tetrakis-O-tert-butyldimethylsilyl-β-d-glucopyranosyl)-3,4,6-tris-O-tert-butyldimethylsilyl-1-thio-β-d-glucopyranoside, produced a highly β-selective glycosidation up to α/β = 2/98 using MeOTf as the activator and 2,6-lutidine as an additive. The ring conformations of the glucose part in these disaccharide donors were all restricted to 3S1, and the conformation would lead to the stereoselectivity.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol070720b