Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
Chemical Modification of Lactose. XVI. Synthesis of Lacto-N-neohexaose
TSUKASA TAKAMURATAKU CHIBASETSUZO TEJIMA
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Keywords: ^<13>C-NMR
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1981 Volume 29 Issue 2 Pages 587-590

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Abstract

Reaction of 1, 6-anhydro-2, 2', 3, 4'-tetra-O-benzyl-β-lactose (1 mol eq.) with the acetylated oxazoline of N-acetyllactosamine (5 mol eq.) gave the corresponding 1, 6-anhydro-β-tetrasaccharide (3, 24.5%) and hexasaccharides (8, 53.5%). The protecting groups of 3 and 8 were removed by the following series of reactions to provide 6'-N-acetyl-lactosaminyllactose (7) and lacto-N-neohexaose (12), respectively : debenzylation followed by acetylation, acetolysis, and de-O-acetylation. 13C-NMR spectral data for 1, 6-anhydro-β-derivatives of 7 and 12 are presented.

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