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Synthesis of [R-(R∗,S∗)]- and [S-(R∗,R∗)]β-hydroxy-3-(β-d-ribofuranosyl)-wybutines, the most probable alternatives for the hypermodified nucleoside of rat liver phenylalanine transfer ribonucleic acid

✍ Scribed by Taisuke Itaya; Tae Kanai; Takehiko Iida

Publisher: Elsevier Science
Year: 1997
Tongue: French
Weight: 213 KB
Volume: 38
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(97)00253-0

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✦ Synopsis

The synthesis of the title compounds started with the Vilsmeier reaction of 3-[2,3,5-tris-O-(tert-butylalmethylsilyl)-~-D-ribofuranosyl]wye (b'b) and proceeded through the Wittig reaction with (R)-N-(methoxyearbonyl)-3-(triphenylphosphonio)alaninate (4), methylation with trimethyisilyldiazomethane, OsO4 oxidation, cyclocondensation with triphosgene, and catalytic hydrogenolysis. Chromalographie separation of the resulting diastereomeric mature and subsequent deprotection afforded the two desired nucleosides [[R-(R*,S*)]-and [S.(R*,R*)]-2b] for the first time.

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