Regiospecific syntheses of N-acetyllactosamine derivatives and application toward a highly practical synthesis of Lewis X trisaccharide

Article abstract of DOI:10.1080/07328309908544034

An efficient methodology for regiospecific glycosylation was developed by using 6-O-tert-butyldiphenylsilyl N-acetylglucosamine derivatives 3 and 5 which bear two free hydroxyl groups as acceptors. The regiospecificity was attributed to the presence of the tert-butyldiphenylsilyl group at the O-6 position of the N-acetylglucosamine derivatives. Glycosylation of suitably protected galactoside donors 10-14 with acceptors 3 and 5 gave only β(1→4) linked disaccharides 15-19 in good yields. Fucosylation of disaccharide 18 led to Lewis X (Le^x) trisaccharide 21 in high yield.

Full text of DOI:10.1080/07328309908544034

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Journal of Carbohydrate Chemistry
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Regiospecific Syntheses of N-
Acetyllactosamine Derivatives
and Application Toward a Highly
Practical Synthesis of Lewis X
Trisaccharide
Zhonghong Gan , Suoding Cao , Qingquan Wu & René Roy
a Department of Chemistry , University of Ottawa , Ottawa,
ON, Canada K1N 6N5
b Department of Chemistry , University of Ottawa , Ottawa,
ON, Canada K1N 6N5
c Department of Chemistry , University of Ottawa , Ottawa,
ON, Canada K1N 6N5
d Department of Chemistry , University of Ottawa , Ottawa,
ON, Canada K1N 6N5
Published online: 27 Feb 2008.
To cite this article: Zhonghong Gan , Suoding Cao , Qingquan Wu & René Roy (1999)
Regiospecific Syntheses of N-Acetyllactosamine Derivatives and Application Toward a Highly
Practical Synthesis of Lewis X Trisaccharide, Journal of Carbohydrate Chemistry, 18:7, 755-773,
DOI: 10.1080/07328309908544034
To link to this article: http://dx.doi.org/10.1080/07328309908544034
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