6044-27-5Relevant articles and documents
Chemical glucosylation of pyridoxine
Bachmann, Thomas,Rychlik, Michael
, (2020/02/13)
The chemical synthesis of pyridoxine-5′-β-D-glucoside (5′-β-PNG) was investigated using various glucoside donors and promoters. Hereby, the combination of α4,3-O-isopropylidene pyridoxine, glucose vested with different leaving and protecting groups and the application of stoichiometric amounts of different promoters was examined with regards to the preparation of the twofold protected PNG. Best results were obtained with 2,3,4,6-tetra-O-acetyl-D-glucopyranosyl fluoride and boron trifluoride etherate (2.0 eq.) as promoter at 0 °C (59%). The deprotection was accomplished stepwise with potassium/sodium hydroxide in acetonitrile/water followed by acid hydrolysis with formic acid resulting in the chemical synthesis of 5′-β-PNG.
Revisiting the armed-disarmed concept rationale: S-benzoxazolyl glycosides in chemoselective oligosaccharide synthesis
Kamat, Medha N.,Demchenko, Alexei V.
, p. 3215 - 3218 (2007/10/03)
(Chemical Equation Presented) It has been discovered that 2-O-benzyl-3,4,6-tri-O-acyl SBox glycosides are significantly less reactive than even "disarmed" peracylated derivatives. This finding has been applied to the synthesis of various oligosaccharides,
S-benzoxazolyl (SBox) glycosides as novel, versatile glycosyl donors for stereoselective 1,2-cis glycosylation
Demchenko, Alexei V.,Malysheva, Nelli N.,De Meo, Cristina
, p. 455 - 458 (2007/10/03)
(Matrix presented) Novel glycosyl donors, S-benzoxazolyl (SBox) glycosides, have been synthesized, tested toward various protecting group manipulations, and applied to the highly stereoselective 1,2-cis glycosylation. These compounds fulfill the requireme