Synthesis of iminoalditol and N-alkyl iminoalditol derivatives of ribopyranosides

被引：6

作者：

Wu, An-Tai ^{[1
]}

Wu, Pey-Jiuann ^{[1
]}

Zou, Wei ^{[2
]}

Chir, Jiun-Ly ^{[3
]}

Chang, Yuan-Chun ^{[1
]}

Tsai, Shuan-Yi ^{[1
]}

Guo, Chao-Qi ^{[1
]}

Chang, Wei-Shuan ^{[1
]}

Hsieh, Yu-Chi ^{[1
]}

机构：

[1] Natl Changhua Univ Educ, Dept Chem, Changhua 50058, Taiwan

[2] Natl Res Council Canada, Inst Biol Sci, Ottawa, ON K1A 0R6, Canada

[3] Acad Sinica, Inst Mol Biol, Taipei 115, Taiwan

来源：

CARBOHYDRATE RESEARCH | 2008年 / 343卷 / 17期

关键词：

Aza-C-glycoside; Iminoalditols; N-Alkylation; Amidation; Michael addition;

D O I：

10.1016/j.carres.2008.08.005

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

Iminoalditol analogs of ribopyranosides were prepared by reduction of a vinylogous urethane intermediate formed from methyl 2-C-(5-O-methanesulfonyl-beta-D-ribofuranosyl)acetate (1) by treatment with sodium azide in DMF at reflux. The N-alkylated analogs were synthesized either by N-alkylation of the corresponding parent iminoaldithol or, more efficiently, from the product of the reaction of 1 with various alkylamines. The latter process involves an S(N)2 substitution at C-5 by the amine followed by an intramolecular hetero-Michael reaction under basic conditions. The 'aglycon' of the iminoalditol was also modified through amidation and esterification. (C) 2008 Elsevier Ltd. All rights reserved.

引用

页码：2887 / 2893

页数：7

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