Synthesis of (S-(−)-wybutine, the fluorescent minor base from yeast phenylalanine transfer ribonucleic acids
✍ Scribed by Taisuke Itaya; Akemi Mizutani
- Publisher
- Elsevier Science
- Year
- 1985
- Tongue
- French
- Weight
- 289 KB
- Volume
- 26
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
The Wittig reaction of l-benzyl-7-formylwye
amino] ethyl] triphenylphosphonium chloride (8) followed by successive methylation and reduction gave (-) -wybutine
📜 SIMILAR VOLUMES
R-(i?\*,S\*) I-E-Hydroxywybutine (8) and its [S-(R\*,R\*)]-isomer (9) have been synthesized as the most probable alternatives for hydroxy-Y base isolated from rat liver phenylalanine tRNA.
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,