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与炭疽四糖相关的寡聚鼠李二糖和三糖的从头不对称合成。

De novo asymmetric synthesis of oligo-rhamno di- and tri-saccharides related to the anthrax tetrasaccharide.

作者信息

Wang Hua-Yu Leo, Guo Haibing, O'Doherty George A

机构信息

College of Nuclear Technology, Chemistry and Biology, Hubei University of Science and Technology, Xianning, Hubei 437100, China ; Department of Chemistry and Chemical Biology, Northeastern University, 360 Huntington Avenue, Boston, MA 02115, USA.

出版信息

Tetrahedron. 2013 Apr 22;69(16):3432-3436. doi: 10.1016/j.tet.2013.02.073.

DOI:10.1016/j.tet.2013.02.073
PMID:23794755
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC3686126/
Abstract

An asymmetric synthesis of the di- and trisaccharide portion of the naturally occurring anthrax tetrasaccharide from acetylfuran has been developed. The construction of the di- and trisaccharide subunits is based upon our previously disclosed route to anthrax tetrasaccharide. The approach uses iterative diastereoselective palladium-catalyzed glycosylations, Luche reductions, diastereoselective dihydroxylations, and regioselective protections for the assembly of the rhamno- di- and tri-saccharide. The route was also modified for the preparation of the mixed D-/L-disaccharide analogue.

摘要

已开发出一种从乙酰呋喃不对称合成天然存在的炭疽四糖的二糖和三糖部分的方法。二糖和三糖亚基的构建基于我们先前公开的合成炭疽四糖的路线。该方法使用迭代的非对映选择性钯催化糖基化、吕歇还原、非对映选择性二羟基化以及区域选择性保护来组装鼠李糖二糖和三糖。该路线也经过修改以制备混合的D-/L-二糖类似物。

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De novo asymmetric synthesis of all-D-, all-L-, and D-/L-oligosaccharides using atom-less protecting groups.使用无原子保护基对全 D-、全 L-和 D/L-低聚糖进行从头不对称合成。
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