ChemInform Abstract: Utilization of Sugars in Organic Syntheses. Part 30. Thio-Sugars. Part 1. Radical-Promoted Thione-Thiol Rearrangement of Cyclic Thionocarbonates: Synthesis of 5-Thioglucose.

✍ Scribed by Y. TSUDA; Y. SATO; K. KANEMITSU; S. HOSOI; K. SHIBAYAMA; K. NAKAO; Y. ISHIKAWA

• Publisher: John Wiley and Sons
• Year: 2010
• Weight: 34 KB
• Volume: 28
• Category: Article
• ISSN: 0931-7597
• DOI: 10.1002/chin.199711188

✦ Synopsis

Utilization of Sugars in Organic Syntheses. Part 30. Thio-Sugars. Part 1. Radical-Promoted Thione-Thiol Rearrangement of Cyclic Thionocarbonates: Synthesis of 5-Thioglucose.

-The title rearrangement is investigated in detail under different reaction conditions. If trialkylsilanes are used as reagents instead of the rearranged compounds only reduction products are obtained. Starting with compound (XIII), whose structure is determined by X-ray analysis, the synthesis of the thioglucose derivative (XVI) is performed. -(TSUDA, Y.;