Glycosylation with N-Troc-protected glycosyl donors
Glycosylation with N-Troc-protected glycosyl donors
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DOI：
10.1016/0008-6215(95)00318-5
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发表时间：
1996-01-11
影响因子：
3.1
通讯作者：
Magnusson, G
中科院分区：
文献类型：
--
作者：
Ellervik, U;Magnusson, G
将 N-Troc 保护的（Troc = 2,2,2-三氯乙氧基羰基）葡萄糖胺和半乳糖胺糖基供体（1-O-乙酰糖、溴糖和硫代糖苷）与相应的 N-Phth 保护的衍生物在 2-（三甲基硅基）乙醇、2-溴乙醇、3-巯基丙酸甲酯、 N-Fmoc-保护的丝氨酸和2-(三甲基甲硅烷基)乙基6-O-苄基-2-脱氧-2-邻苯二甲酰亚胺基-β-D-吡喃葡萄糖苷。 N-Troc 保护的供体以比 N-Phth 保护的对应物更高的产率产生纯 β-糖苷。 N-Troc 保护基团可以通过锌还原来去除，这样可以在含有 N-Troc 和 N-Phth 基团的寡糖中进行选择性 N-脱保护。
N-Troc-protected (Troc = 2,2,2-trichloroethoxycarbonyl) glucosamine and galactosamine glycosyl donors (1-O-acetyl sugar, bromo sugar, and thioglycoside) were compared with the corresponding N-Phth-protected derivatives in glycosylations of 2-(trimethylsilyl)ethanol, 2-bromoethanol, methyl 3-mercaptopropionate, N-Fmoc-protected serine, and 2-(trimethylsilyl)ethyl 6-O-benzyl-2-deoxy-2-phthalimido-beta-D-glucopyranoside. The N-Troc-protected donors gave pure beta-glycosides in somewhat higher yields than the N-Phth-protected counterparts. The N-Troc protecting group can be removed by reduction with zinc, which allows selective N-deprotection in oligosaccharides containing both N-Troc and N-Phth groups.