ChemInform Abstract: Cycloaddition of Acetylenes with 5-Azido-5-deoxy-D-aldopentose Derivatives: Synthesis of Triazole Reversed Nucleoside Analogues.

✍ Scribed by P. NORRIS; D. HORTON; B. R. LEVINE

• Publisher: John Wiley and Sons
• Year: 2010
• Weight: 29 KB
• Volume: 28
• Category: Article
• ISSN: 0931-7597
• DOI: 10.1002/chin.199717224

✦ Synopsis

Cycloaddition of Acetylenes with 5-Azido-5-deoxy-D-aldopentose Derivatives: Synthesis of Triazole Reversed Nucleoside Analogues.

-1,3-Dipolar cycloaddition of carbohydrate derived azides such as (I) to phenylacetylene provides a single regioisomeric triazole (III), whereas ethyl propiolate yields two cycloadducts (V) and (VI). The major isomers (cf. (V)) are precursors of reversed nucleoside analogues (VIII). -(NORRIS, P.;