Diastereoselective synthesis of branched 2-deoxy sugars via radical c-c bond formation reactions

✍ Scribed by Bernd Giese; Kay Gröninger

• Book ID: 104233648
• Publisher: Elsevier Science
• Year: 1984
• Tongue: French
• Weight: 201 KB
• Volume: 25
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)81279-x

✦ Synopsis

From glycals l and 5, 2-deoxy sugars can be synthesized in 40-728 yields. With 1,2_disubstituted alkenes 1 this radical C-C bond formation reaction leads with high stereoselectivity to the isomers The formation of C-C bonds via solvomercuration of electron-rich alkenes and reduction with hydrides in the presence of electron-poor alkenes is a new versatile method 1)

2. for the synthesis of target molecules . We have now shown that this method can also be applied to carbohydrate chemistry. Solvomercuration of the galactal 1 leads, in a stereospecific reaction, to the organomercuric salt 23'. In situ reduction of 2 with boro or tin hydrides (HM) in the presence of