期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 79, 期 6, 页码 2611-2624出版社
AMER CHEMICAL SOC
DOI: 10.1021/jo500032k
关键词
-
资金
- National Institutes of Health [GM-06982]
- National Science Foundation [CHE-0957738]
- Royal Thai government
In this article, we evaluate glycosyl dithiocarbamates (DTCs) with unprotected C2 hydroxyls as donors in beta-linked oligosaccharide synthesis. We report a mild, one-pot conversion of glycals into beta-glycosyl DTCs via DMDO oxidation with subsequent ring opening by DTC salts, which can be generated in situ from secondary amines and CS2. Glycosyl DTCs are readily activated with Cu(I) or Cu(II) triflate at low temperatures and are amenable to reiterative synthesis strategies, as demonstrated by the efficient construction of a tri-beta-1,6-linked tetrasaccharide. Glycosyl DTC couplings are highly beta-selective despite the absence of a preexisting C2 auxiliary group. We provide evidence that the directing effect is mediated by the C2 hydroxyl itself via the putative formation of a cis-fused bicyclic intermediate.
作者
我是这篇论文的作者
点击您的名字以认领此论文并将其添加到您的个人资料中。
推荐
暂无数据