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
JOURNAL FREE ACCESS

1981 Volume 29 Issue 8 Pages 2270-2276

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