4.5 Article

Sialylation using N-glycolylneuraminyl phosphite donors to synthesize Neu5Gc-containing glycans

Journal

CARBOHYDRATE RESEARCH
Volume 344, Issue 8, Pages 959-965

Publisher

ELSEVIER SCI LTD
DOI: 10.1016/j.carres.2009.03.004

Keywords

N-Glycolylneuraminic acid; Sialic acid; Glycosylation; Phosphite

Funding

  1. Ministry of Education, Science, Sports and Culture, Japan
  2. Japan Society for the Promotion of Science [20710171]
  3. Grants-in-Aid for Scientific Research [20710171] Funding Source: KAKEN

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Efficient sialylations using N-glycolylneuraminic acid (Neu5Gc) phosphite donors having an acetyl or benzyl group on the glycolyl moiety are described in the synthesis of Neu5Gc-containing glycans. Both phosphite donors 1 and 2 were readily coupled with primary and secondary acceptor alcohols in propionitrile at -78 degrees C to provide the desired glycosides with good alpha-selectivities. (C) 2009 Elsevier Ltd. All rights reserved.

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