A Vicinal Acyloxy Group Participation SN2 Reaction of Thiol Nucleophiles in the Formation of Thioacetals

被引：3

作者：

Wu Qinpei ^{[1
]}

Xi Xiaodong ^{[1
]}

Chen Xi ^{[1
]}

Li Hui ^{[2
]}

Zhang Qingshan ^{[1
]}

机构：

[1] Beijing Inst Technol, Dept Appl Chem & Pharmaceut, Beijing 100081, Peoples R China

[2] Beijing Inst Technol, Dept Chem, Sch Sci, Beijing 100081, Peoples R China

来源：

CHINESE JOURNAL OF CHEMISTRY | 2009年 / 27卷 / 10期

基金：

中国国家自然科学基金;

关键词：

acetal; thioacetal; protecting group; acyl group; 4,5,6-TRI-O-BENZOYL-2,3-DI-S-ETHYL-2,3-DITHIO-D-ALLOSE DIETHYL DITHIOACETAL; BETA-D-MANNOPYRANOSIDES; GLYCOSYLATION REACTIONS; D-XYLOSE; CHEMOSELECTIVE THIOACETALIZATION; OLIGOSACCHARIDE SYNTHESIS; CARBONYL-COMPOUNDS; EFFICIENT; DERIVATIVES; CONVERSION;

D O I：

10.1002/cjoc.200990330

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Thioacetalization of acyl protected furanosides led to products with an ethanethiol group at C-2 and 3-O-acetyl-1,2-di-O-isopropylidene-D-furanoses were converted into corresponding thioacetals with two ethanethiol groups at both C-2 and C-3 positions under the standard thioacetalization conditions. All products were characterized by H-1 NMR, C-13 NMR and HRMS data. X-ray structure analysis indicates that the vicinal acyloxy group is stereoselectively substituted by ethanethiols. The supposed mechanisms for these two kinds of transformations were presented.

引用

页码：1962 / 1966

页数：5

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