Chemical Modification of Lactose. XV. Syntheses of O-α- and O-β-L-Fucopyranosyl-(1→3)-O-β-D-galactopyranosyl-(1→4)-D-glucopyranoses (3'-O-α- and 3'-O-β-L-Fucopyranosyllactoses)
スポンサーリンク
概要
- 論文の詳細を見る
1,6-Anhydro-4', 6'-O-benzylidene-3'-O-tosyl-β-lactose was converted into 1,6-anhydro-2,2', 3-tri-O-benzyl-4', 6'-O-benzylidene-β-lactose (3) in 74.1% yield by benzylation followed by detosylation. Condensation of 3 with 2,3,4-tri-O-acetyl-α-L-fucopyranosyl bromide in benzene-nitromethane in the presence of mercuric cyanide and molecular sieves gave the corresponding trisaccharide derivatives (6 and 11) bearing α- and β-L-fucopyranosyl linkages in 37.1 and 43.1% yields, respectively. Compounds 6 and 11 were isolated by column chromatography on silica gel. The title sugars (10 and 15) were prepared in 4 steps from 6 and 11,respectively ; hydrogenolytic removal of the benzylidene and benzyl groups, acetylation, cleavage of the 1,6-anhydro-β-ring to β-acetate, and deacetylation. ^1H-NMR and ^<13>C-NMR spectral data of 10,15,and the intermediates are also described.
- 公益社団法人日本薬学会の論文
- 1981-04-25
著者
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手島 節三
名古屋市立大学薬学部
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高村 吏
Faculty of Pharmaceutical Sciences, Nagoya City University
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千葉 拓
Faculty of Pharmaceutical Sciences, Nagoya City University
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高村 吏
Research And Development Division General Laboratory Arakawa Chotaro & Co.
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千葉 拓
名古屋市立大学薬学部
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