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. 2007 Nov 9;72(23):8958-61.
doi: 10.1021/jo701694k. Epub 2007 Oct 16.

Syntheses of Lewis(x) and dimeric Lewis(x): construction of branched oligosaccharides by a combination of preactivation and reactivity based chemoselective one-pot glycosylations

Adeline Miermont  1 , Youlin Zeng, Yuqing Jing, Xin-shan Ye, Xuefei Huang
Affiliations

Syntheses of Lewis(x) and dimeric Lewis(x): construction of branched oligosaccharides by a combination of preactivation and reactivity based chemoselective one-pot glycosylations

Adeline Miermont et al. J Org Chem. .

Abstract

Two asymmetrically branched oligosaccharides, LewisX and dimeric LewisX, were assembled in one pot with high yields and exclusive regio- and stereoselectivities. p-Tolyl thioglycosides were utilized as the sole type of building blocks, thus simplifying the overall synthetic design. The reactivity-independent nature of the preactivation based method allows modular assembly of the dimeric LewisX octasaccharide without the need for tedious protective group manipulation to achieve exact anomeric reactivities.

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Figures

Scheme 1
Scheme 1
Deprotection of LewisX and Dimeric LewisX
See this image and copyright information in PMC

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