- Glycosyl Imidates, 10. - Glycosyl Phosphates from Glycosyl Trichloroacetimidates
-
The glycosyl trichloroacetimidates 1-α,β, 8-α, 11-α, 13-α, 15-α, and 17-α directly transfer the glycosyl moiety to phosphoric acid mono- and diesters.The acidity of the phosphoric acid derivatives used was sufficient for the activation of the trichloroacetimidates, therefore an additional acidic catalyst was not required.From the β-imidate 1-β α-glycosyl phosphate and from the α-imidates preferentially β-glycosyl phosphates were obtained.Reaction of dibenzyl phosphate (2a) and cetyl phosphate (2c) with 1-α demonstrated that β/α-anomerization iscatalyzed by traces of acid.The glycosyl phosphates 3a-α, 3a-β - 3c-β, 3f-α, 9a-β, and 9c-β were partly or totally deprotected.The structures of the synthezised compounds were assigned by 1H NMR spectroscopy and by comparison with literature data.
- Schmidt, Richard R.,Stumpp, Michael
-
p. 680 - 691
(2007/10/02)
-
- α- and β-D-GLUCOPYRANOSYL PHOSPHATES from O-α-D-GLUCOPYRANOSYL TRICHLOROACETIMIDATES
-
β-D-Glucopyranosylphosphates were obtained in high yields from O-α-D-glucopyranosyl trichloroacetimidates 2a-c and phosphoric acid monoesters and diesters 5-10.Some β-phosphates were transformed into the corresponding α-derivatives by acid catalysis.
- Schmidt, Richard R.,Stumpp, Michael,Michel, Josef
-
p. 405 - 408
(2007/10/02)
-