Preparation of selenoanhydro- and telluroanhydroglycofuranosides and some corresponding nucleosides

被引：19

作者：

Adiwidjaja, G

Schulze, O

Voss, J

Wirsching, J

机构：

[1] Univ Hamburg, Inst Organ Chem, D-20146 Hamburg, Germany

[2] Univ Hamburg, Mineral Petrograph Inst, D-20146 Hamburg, Germany

来源：

CARBOHYDRATE RESEARCH | 2000年 / 325卷 / 02期

关键词：

2-seleno-2,5-anhydro-D-arabinofuranosides; 3-seleno-3,5-anhydro-D-xylofuranosides; 2-telluro-2,5-anhydro-alpha-D-arabinofuranoside; X-ray structural analysis; 2-seleno-2,5-anhydro-alpha-D-arabinofuranosyl nucleosides;

D O I：

10.1016/S0008-6215(99)00321-3

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：

Methyl 2,3-anhydro-alpha-D-ribofuranoside (3a) was transformed into methyl 2-seleno-2,5-anhydro-alpha-D-arabinofuranoside (5a) and methyl 3-seleno-3,5-anhydro-alpha-D-xylofuranoside (6a) in two steps via the reaction of the C-5 mesylate of 3a, methyl 2,3-anhydro-5-O-mesyl-alpha-D-ribofuranoside (4a), with sodium hydrogen selenide. The corresponding beta anomer of 3a yielded methyl 3-seleno-3,5-anhydro-beta-D-xylofuranoside as the main product and only traces of methyl 2-seleno-2,5-anhydro-beta-D-arabinofuranoside. Sodium hydrogen telluride transformed 4a into methyl 2-telluro-2,5-anhydro-alpha-D-arabinofuranoside Starting from 5a we prepared 1-(2-seleno-2,5-anhydro-alpha-D-arabinofuranosyl)uracil and the analogous thymidine nucleoside. Compound 6a could not be transformed into nucleosides. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：107 / 119

页数：13

共 23 条

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