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一种用于将4,6-O-亚苄基缩醛串联开环为其相应的6-O-乙酰基衍生物的无金属温和绿色方法:在一锅糖基化反应合成三糖中的应用。

A metal free mild and green approach for tandem opening of 4,6-O-benzylidene acetals to their corresponding 6-O-acetyl derivatives: Application in the synthesis of a trisaccharide using one-pot glycosylation reactions.

作者信息

Mukherjee Mana Mohan, Basu Nabamita, Nandi Shantanu, Ghosh Rina

机构信息

Department of Chemistry, Jadavpur University, Jadavpur, Kolkata, 700032, West Bengal, India.

Department of Chemistry, Nabagram Hiralal Paul College, Konnagar, Hoogly, West Bengal, 712246, India.

出版信息

Carbohydr Res. 2019 Apr 1;476:36-43. doi: 10.1016/j.carres.2019.03.002. Epub 2019 Mar 14.

DOI:10.1016/j.carres.2019.03.002
PMID:30889504
Abstract

An efficient and high yielding reaction for tandem opening of 4,6-O-benzylidene derivatives (gluco, galacto, manno, 2-phthalimido-2-deoxy glucosides) to their corresponding 6-O-acetyl derivatives has been established under metal free condition using 60% solution of aqueous acetic acid (v/v). The reaction is equally pertinent for large scale synthesis and also for disaccharide glycosides. Its application for the construction of a building block towards synthesis of a trisaccharide part related to Pseudomonas aeruginosa utilizing one-pot glycosylation reactions has also been described.

摘要

在无金属条件下,使用60%的乙酸水溶液(v/v),已建立了一种高效高产的反应,可将4,6-O-亚苄基衍生物(葡萄糖、半乳糖、甘露糖、2-邻苯二甲酰亚氨基-2-脱氧葡萄糖苷)串联开环转化为相应的6-O-乙酰基衍生物。该反应同样适用于大规模合成以及二糖糖苷。还描述了其在利用一锅法糖基化反应构建用于合成与铜绿假单胞菌相关的三糖部分的结构单元中的应用。

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