- Reliable synthesis of various nucleoside diphosphate glycopyranoses
-
A reliable and high yielding synthetic pathway for the synthesis of the biologically highly important class of nucleoside diphosphate sugars (NDP-sugars) was developed by using various cycloSal-nucleotides 1 and 9 as active ester building blocks. The reaction with anomerically pure pyranosyl1-phosphates 2 led to the target NDP-sugars 20-45 in a nucleophilic displacement reaction, which cleaves the cycloSal moiety in anomerically pure forms. As nucleosides cytidine, uridine, thymi-dine, adenosine, 2′-deoxy-guanosine and 2′,3′-dideoxy-2′,3′- didehydrothymidine were used while the phosphates of D-glucose, D-galactose, D-mannose, DNAc-glucosamine, D-NAc-galactosamine, D-fucose, L-fucose as well as 6deoxy-D-gulose were introduced.
- Wolf, Saskia,Zismann, Tanja,Lunau, Nathalie,Meier, Chris
-
scheme or table
p. 7656 - 7664
(2010/03/26)
-
- Efficient synthesis of nucleoside diphosphate glycopyranoses
-
(Chemical Equation Presented) Short and sweet: A new, short synthetic pathway for the synthesis of the enormously important class of nucleoside diphosphate sugars (NDP sugars) was developed using cyclo-saligenyl (cycloSal) nucleosyl phosphate triesters as
- Wendicke, Silke,Warnecke, Svenja,Meier, Chris
-
p. 1500 - 1502
(2008/12/22)
-
- Syntheses of glycosyl phosphates by phase transfer catalysis
-
The peracetylated glycosyl bromides of D-glucose (1), D-galactose (2), and D-lactose (5) were treated with dibenzyl phosphate in a catalytic two-phase system using tetrabutylammonium hydrogen sulfate as catalyst.The reactions proceeded by complete inversi
- Roy, Rene,Tropper, Francois D.,Grand-Maitre, Chantal
-
p. 1462 - 1467
(2007/10/02)
-
- 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)
-