A Stereoselective Approach for the Synthesis of α-Sialosides
- 19 July 2001
- journal article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 66 (16) , 5490-5497
- https://doi.org/10.1021/jo010345f
Abstract
A highly efficient synthesis of the human melanoma associated antigen GD(3) derivative has been described. A key feature of the synthetic approach was the use of sialyl donors that were protected with a C-5 trifluoroacetamide moiety. These sialyl donors gave high yields and excellent alpha-anomeric selectivities in direct glycosylations with a wide variety of glycosyl acceptors ranging from C-8 hydroxyls of sialic acids and C-3 hydroxyls of galactosides to reactive primary alcohols.Keywords
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