Synthesis of 3-(β-D-ribofuranosyl)-2-fluoropyridine and 3-(β-D-ribofuranosyl)-pyridin-2-one
✍ Scribed by Jasenka Matulic-Adamic; Leonid Beigelman
- Publisher
- Elsevier Science
- Year
- 1997
- Tongue
- French
- Weight
- 224 KB
- Volume
- 38
- Category
- Article
- ISSN
- 0040-4039
No coin nor oath required. For personal study only.
✦ Synopsis
Pyridin-2-one C-nucleoside 13 was prepared in 7 steps from 2-fluoropyridine 1 and D-ribono-l,4-1actone 2. The successful approach to ~i-ribofuranosides 12 and 13 consisted of the reductive opening of the furanose ring of hemiacetal 3 followed by intramolecular Mitsunobu cyclization.
📜 SIMILAR VOLUMES
An unnatural base pair, 2-amino-6-(N,N-dimethylamino)purine (denoted x) and pyridin-2-one (denoted y), was designed to prove the structural requirements for base pair formation involving shape complementarity. It was expected that y might satisfy the structural requirements for pairing with x, in wh
Pyridin-2-one C-nucleoside 2 was prepared using several different approaches. The most efficient pathway utilized the condensation of 2,3,5-tri-O-benzyl-D-ribono-l,4lactone (4) and 2-(benzyloxy)-5-bromopyridine (5), followed by deoxygenation with Et3SiH/BF3.Et20 and removal of the benzyl protecting
## 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