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
ChemInform Abstract: Synthesis of 2′,5′-Dideoxy-5′-Substituted Pyrimidine Nucleosides via Intramolecular Glycosylation.
✍ Scribed by Hideyuki Sugimura; Yoshiko Katoh
- Publisher
- John Wiley and Sons
- Year
- 2010
- Weight
- 31 KB
- Volume
- 30
- Category
- Article
- ISSN
- 0931-7597
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✦ Synopsis
Synthesis of 2',5'-Dideoxy-5'-Substituted Pyrimidine Nucleosides via Intramolecular Glycosylation.
-5'-Azido and 5'-arylthio-5-deoxypyrimidine nucleosides are synthesized employing intramolecular glycosylation, in which a reaction intermediate is treated in situ with an azide salt or thiol. In some cases the eliminated phenylthiolate acts as the nucleophile affording derivative (Va).
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Stereoselective Synthesis of 2',3'-Dideoxy-nucleosides via Intramolecular Glycosylation of Phenyl 1-Seleno-glycosides. Synthesis of 2',3'-Dideoxythymidine. -The intramolecular glycosylation of the coupling products (III) is examined. However, treatment with AgO-Tf and NaOH results only in the isol