Add time:08/25/2019         Source:sciencedirect.com

Methyl 2,3-di-O-benzoyl-6-deoxy-α-l-galactopyranoside (2) was converted into the 4-deoxy-4-iodo-α-l-gluco derivative 4 by triflate-mediated inversion. Catalytic reduction of 4 gave methyl 2,3-di-O-benzoyl-4,6-dideoxy-α-l-xylo-hexopyranoside (6) and subsequent O-debenzoylation gave methyl 4,6-dideoxy-α-l-xylo-hexopyranoside (7). Selective benzoylation of l-fucose gave 1,2,3-tri-O-benzoyl-α-l-fucopyranose (14). An analogous sequence of reactions, based on the inversion of configuration at C-4, yielded 4,6-dideoxy-4-iodo-l-glucopyranose (17) and 4,6-dideoxy-l-xylo-hexopyranose (19). Reaction of the 4-trifluoromethanesulfonate (15) of 14 with sodium fluoride in N,N-dimethylformamide gave 1,2,3-tri-O-benzoyl-6-deoxy-4-O-formyl-α-l-glucopyranose (12) and 1,2,3-tri-O-benzoyl-4,6-dideoxy-α-l-threo-hex-4-enopyranose (13). Treatment of 14 with diethylaminosulfur trifluoride and then O-debenzoylation gave 4,6-dideoxy-4-fluoro-l-glucopyranose (11). Reaction of 15 with sodium iodide in N,N-dimethylformamide gave 1,2,3-tri-O-benzoyl-4,6-dideoxy-4-iodo-α-l-glucopyranose (16). The α-glycosyl bromide (20) derived from 16 reacted stereoselectively with dibenzyl phosphate to give the β-(21) or α-glycosyl dibenzyl phosphate (22).

We also recommend Trading Suppliers and Manufacturers of 1,2,3-TRI-O-BENZOYL-4-DEOXY-ALPHA-L-FUCOPYRANOSE (cas 132867-78-8). Pls Click Website Link as below: cas 132867-78-8 suppliers