Syntheses of LewisX and Dimeric LewisX: Construction of Branched Oligosaccharides by a Combination of Preactivation and Reactivity Based Chemoselective One-Pot Glycosylations
- 16 October 2007
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 72 (23) , 8958-8961
- https://doi.org/10.1021/jo701694k
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.Keywords
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