40591-52-4Relevant academic research and scientific papers
One-step, stereocontrolled synthesis of glycosyl 1-phosphates, uridine- 5'-diphosphogalactose, and uridine-5'-diphosphoglucose from unprotected glycosyl donors
Hanessian, Stephen,Lu, Pu-Ping,Ishida, Hideki
, p. 13296 - 13300 (1998)
The reaction of 2-(1,2-trans-glycopyranosyloxy)-3-methoxypyridines (MOP glycosides) with phosphoric acid leads to the corresponding 1,2-cis-1- phosphates in good yield and excellent stereoselectivity. 1-Phosphate esters of α-D-glucopyranose, α-D-galactopyranose, and 2-azido-2-deoxy-α-D- galactopyranose were thus prepared without recourse to protective groups. In the L-fucose series, the major product was the α-L-fucosyl 1-phosphate. An alternative method that relies on neighboring group participation allowed the preparation of a protected β-L-fucosyl 1-phosphate. Reaction of unprotected β-D-glucopyranosyloxy and β-D-galactopyranosyloxy MOP donors with uridine diphosphoric acid gave UDP-Glc and UDP-Gal with preponderance of the desired α-anomeric configuration.
AN APPROACH TO THE SYNTHESIS OF α-L-FUCOPYRANOSYL PHOSPHORIC MONO- AND DIESTERS VIA PHOSPHITE INTERMEDIATES
Westerduin, P.,Veeneman, G. H.,Marugg, J. E.,Marel, G. A. van der,Boom, J. H. van
, p. 1211 - 1214 (2007/10/02)
The reagent chloro-β-cyanoethyl-N,N-diisopropylamino-phosphoramidite reacts smoothly with the anomeric hydroxyl group of a properly protected (benzyl) α-L-fucopyranose to afford a relatively stable phosphite intermediate in high yield.The latter can easil
