Stereocontrolled Synthesis of Pyridazine, Pyrazine, and Triazine 2'-DEOXY-β-Nucleosides by Means of Intramolecular Glycosylation
✍ Scribed by Sugimura, Hideyuki; Motegi, Miho; Sujino, Keiko
- Book ID
- 121484302
- Publisher
- Taylor and Francis Group
- Year
- 1995
- Tongue
- English
- Weight
- 225 KB
- Volume
- 14
- Category
- Article
- ISSN
- 0732-8311
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📜 SIMILAR VOLUMES
Al~tract: A pyrimidine moiety was tethered at the 3'-~-position of D-threo-furanosides. By carefully controlling the reaction conditions, pyrimidine bases can be delivered to the anomeric center to give of ~-pyrimidine nucleosides in good yield and with complete stereocontrol.
Stereocontrolled Synthesis of β-2'-Deoxypyrimidine Nucleosides via Intramolecular Glycosylations. -In continuation of efforts to develop general methods for the exclusive formation of β-nucleosides, the base-promoted reaction of the pentafuranoside (II) with allyloxypyrimidines (II) is reported. Af
## Abstract Nucleobase‐anion glycosylation of 6‐(methylthio)‐2‐azapurine (1) with 2‐deoxy‐3,5‐di‐__O__‐(p‐toluoyl)‐α‐D‐erythro‐pentofuranosyl chloride (2) yields the 2′‐deoxy‐β‐D‐ribofuranosides 3–5 stereoselectively. The distribution of regioisomers is as follows: N‐9 (32%); N‐2 (30%), and N‐7 (7%