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3-O-(3,6-脱水-β-D-吡喃半乳糖基)-α-D-吡喃半乳糖苷甲酯和3,6-脱水-4-O-β-D-吡喃半乳糖基-α-D-吡喃半乳糖苷甲酯的高效立体选择性合成。

Efficient and stereoselective synthesis of methyl 3-O-(3,6-anhydro-beta-D-galactopyranosyl)-alpha-D-galactopyranoside and methyl 3,6-anhydro-4-O-beta-D-galactopyranosyl-alpha-D-galactopyranoside.

作者信息

Rashid A, Mackie W

机构信息

Department of Biochemistry and Molecular Biology, University of Leeds, Great Britain.

出版信息

Carbohydr Res. 1992 Jan;223:147-55. doi: 10.1016/0008-6215(92)80013-q.

DOI:10.1016/0008-6215(92)80013-q
PMID:1596915
Abstract

Methyl 3-O-(3,6-anhydro-beta-D-galactopyranosyl)-alpha-D-galactopyranoside (3) and methyl 3,6-anhydro-4-O-beta-D-galactopyranosyl-alpha-D-galactopyranoside (4) have been synthesised stereoselectively using three coupling procedures. Acceptable yields were achieved using acetylated derivatives as donors and trimethylsilyl triflate as the catalyst. Intramolecular tosylate displacement to form 3,6-anhydro rings proceeded in methanolic sodium methoxide.

摘要

3-O-(3,6-脱水-β-D-吡喃半乳糖基)-α-D-吡喃半乳糖苷甲酯(3)和3,6-脱水-4-O-β-D-吡喃半乳糖基-α-D-吡喃半乳糖苷甲酯(4)已通过三种偶联方法立体选择性合成。使用乙酰化衍生物作为供体和三甲基甲硅烷基三氟甲磺酸酯作为催化剂可获得可接受的产率。在甲醇钠甲醇溶液中进行分子内对甲苯磺酸酯取代反应以形成3,6-脱水环。

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引用本文的文献

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