A General Method for the Synthesis of C-Glycosides of Nojirimycin

✍ Scribed by Fuchss, Thomas ;Streicher, Hansjörg ;Schmidt, Richard R.

• Publisher: John Wiley and Sons
• Year: 1997
• Tongue: English
• Weight: 803 KB
• Volume: 1997
• Category: Article
• ISSN: 0947-3440
• DOI: 10.1002/jlac.199719970706

✦ Synopsis

Abstract

Methyl 2,3,4,6‐tetra‐O‐acetyl‐N‐(benzyloxycarbonyl)nojirimycin (3) can be readily transformed into the corresponding azaglycal 6 or fluoride 7, which are versatile glycosyl/piperidinosyl donors. Reaction of 7 with allyltrimethylsilane, propinyltrimethylsilane, trimethylsilyl cyanide, and trimethylsilyl enol ether as carbon nucleophiles, afforded, in the presence of BF~3~ · OEt~2~ as catalyst, the corresponding C‐glycosides 8–10 and 12–14 in good yields. The anomeric configurations of the C‐glycosides are ascertained with the help of ROESY‐NMR data.