Synthesis of higher-carbon sugars by tributyltin hydride - azobisisobutyronitrile induced radical additions

✍ Scribed by Younosuke Araki; Tadatoshi Endo; Masaki Tanji; Yoshifusa Arai; Yoshiharu Ishido

• Publisher: Elsevier Science
• Year: 1988
• Tongue: French
• Weight: 239 KB
• Volume: 29
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)86053-0

✦ Synopsis

The Bu3SnH -AIBN induced radical additions of 3,5-di-g-acetyl-6deoxy-6-iodo-l,Z-O-isopropylidene-a-B_gluco-and -allofuranose (I and lo), and methyl 5-deoxy-5-~odo-2,3-O-isopropylidene-8-B-ribofuranoside (19) to dimethyl maleate, methyl acrylate, acrylonitrile, methyl vinyl ketone, and vinylene carbonate gave various types of higher-carbon sugars.

Higher-carbon sugars were found in nature as important substructural units of various types of antibiotics such as hikizimycin, 2 apramycin, 3 tunicamytin, 4 and mildiomycin. 5

Valuable and interesting biological properties of