Preparation of selenoanhydro- and telluroanhydroglycofuranosides and some corresponding nucleosides

• Published in: Carbohydrate research 2000-04, Vol.325 (2), p.107-119
• Main Authors: Adiwidjaja, Gunadi, Schulze, Oliver, Voss, Jürgen, Wirsching, Jörn
• Format: Article
• Language: English
• Subjects: 2-Seleno-2,5-anhydro- d-arabinofuranosides; 2-Seleno-2,5-anhydro-α- d-arabinofuranosyl nucleosides; 2-Telluro-2,5-anhydro-α- d-arabinofuranoside; 3-Seleno-3,5-anhydro- d-xylofuranosides; Carbohydrate Sequence; Crystallography, X-Ray; Glycosides - chemistry; Magnetic Resonance Spectroscopy; Models, Chemical; Models, Molecular; Molecular Sequence Data; Nucleosides - chemical synthesis; X-ray structural analysis
• ISSN: 0008-6215; 1873-426X
• DOI: 10.1016/S0008-6215(99)00321-3

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