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A General Method for the Synthesis of C‐Glycosides of Nojirimycin
Author(s) -
Fuchss Thomas,
Streicher Hansjörg,
Schmidt Richard R.
Publication year - 1997
Publication title -
liebigs annalen
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0947-3440
DOI - 10.1002/jlac.199719970706
Subject(s) - chemistry , anomer , nucleophile , glycoside , trimethylsilyl , glycosyl , organic chemistry , enol , enol ether , fluoride , catalysis , stereochemistry , medicinal chemistry , inorganic chemistry
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.