Synthesis of 5-(β-D-ribofuranosyl)-pyridin-2-one: A “deletion-modiffied” analogue of uridine
✍ Scribed by Jasenka Matulic-Adamic; Leonid Beigelman
- Publisher
- Elsevier Science
- Year
- 1997
- Tongue
- French
- Weight
- 230 KB
- Volume
- 38
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
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 groups.
📜 SIMILAR VOLUMES
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.
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
Synthesis of 5-Hydroxy-2-(β-D-ribofuranosyl)pyran-4-one from a Pyranulose Glycoside. -The title compound (VI) is synthesized from the pyranulose glycoside (I) by bromination, acetylation with Ac 2 O, and final deprotection with ammonia. -(KANAZAWA, SHIGEYUKI; MIZUNO,