Investigations of the mechanism of nucleoside synthesis. I. 13C-NMR studies of dihydro-s-triazine-SnCl4 complexes

✍ Scribed by W. Wierenga; H.I. Skulnick

• Publisher: Elsevier Science
• Year: 1979
• Tongue: French
• Weight: 279 KB
• Volume: 20
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)95482-6

✦ Synopsis

C-NAB has been employed to demonstrate and define the nature of Snmoctahedral compZexes of bissilyt triusines as a further investigation of nucleoside condensation mechanisms.

We have been intrigued by some observations relating to earlier chemistry from this laboratory involving the Lewis acid mediated condensation of the silylated dihydro-s-triazine 1 with the deoxy. ribosyl chloride 2 in the synthesis of the antiviral, -antibiotic dihydro-5-azathymidine, 2. These observations included (1) that the nucleoside anomeric ratio changed as a function of reaction temperature, (2) that the ratio of Lewis acid "catalyst" (SnCl&) to triazine was approximately 1:2 for optimum yield, and (3) that deoxyribosyl chloride decomposition was not observed when the triazine and SnCl& were premixed in the optimum ratio. We are independently examining several aspects of this chemistry and report herein our findings involving the interaction of SnClk with 1_.