Stereoselective Synthesis of Oligo-α-(2,8)-Sialic Acids
- 13 May 2006
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 128 (22) , 7124-7125
- https://doi.org/10.1021/ja0613613
Abstract
An efficient and elegant synthesis of α(2,8)-oligosialosides is described. The 5-N,4-O-carbonyl-protected sialyl donor undergoes α-sialylation in CH2Cl2 to give α(2,8)- and α(2,9)-disialosides in excellent yields. The 5-N,4-O-carbonyl protecting group was effective in improving the reactivity of the C8 hydroxyl groups toward glycosylation. Using the sialyl building block, the synthesis of tetra-α(2,8)-sialic acid was accomplished by using a simple glycosidation and deprotection protocol.Keywords
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