Total synthesis of 2-(β-D-ribofuranosyl)thiazole-4-carboxamide (Tiazofurin) and of precursors of ribo-C-nucleosides
✍ Scribed by R. Mampuya Bimwala; Pierre Vogel
- Publisher
- John Wiley and Sons
- Year
- 1989
- Tongue
- German
- Weight
- 637 KB
- Volume
- 72
- Category
- Article
- ISSN
- 0018-019X
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## Abstract A new protected 2‐deoxy‐D‐ribose derivative, 5‐__O__‐[(__tert__‐butyl)diphenylsilyl]‐2‐deoxy‐3,4‐__O__‐ isopropylidene‐__aldehydo__‐D‐ribose (5), was synthesized starting from 2‐deoxy‐D‐ribose. This compound was coupled with 2‐lithio‐4‐(4,5‐dihydro‐4,4‐dimethyloxazol‐2‐yl)pyridine givin
Metallation of 5-ethynyl-1-(2,3,5-tri-O-terf-butyldimethylsilyl-~-~-ribof~anosyl)imidazole-4-carboxamide (1) using n-BuLi, deuteration with deuterium oxide and removal of the fertbutyldimethylsilyl protecting groups using tetrabutylammonium fluroide yielded [2-'H]-5ethynyl-1 -(~-D-ribofi1ranosyl)imi