The β-Form of the Cori Ester (d-Glucopyranose 1-Phosphate)

Natural phosphoglycans containing glycosyl phosphate units: structural diversity and chemical synthesis

“…230 The (1!6)-linked tri(N-acetyl-D D-mannosaminyl) diphosphate 208 (Scheme 18), representing a fragment of the capsular antigen from N. meningitidis serogroup A (Section 2.1), was synthesised by Pozsgay and coworkers 231 from the 2-azido-2-deoxy-D D-mannosyl H-phosphonate derivative 201 and the monohydroxyl derivative 202, using benzyl ethers for permanent Oprotection and 6-O-acetyl as a temporary protecting group. Two consecutive chain extensions provided the protected dimeric (203) and trimeric (206) fragments in high yields. The 2-azido group was reduced, followed in turn by N-acetylation, in each of these derivatives prior to removal of the O-acetyl protecting group.…”

One-Step, Stereocontrolled Synthesis of Glycosyl 1-Phosphates, Uridine-5‘-diphosphogalactose, and Uridine-5‘-diphosphoglucose from Unprotected Glycosyl Donors

“…The chemical synthesis of glycosyl 1-phosphates has relied on multistep procedures in which an O -acetylated glycosyl halide is condensed with a salt of phosphoric acid or its ester, followed by de-esterification. For example, treatment of tetra- O -acetyl-α- d -glycopyranosyl bromide with trisilver phosphate or silver diphenyl phosphate in refluxing benzene gives, after a tedious purification protocol, α- d -glucosyl 1-phosphate (α- d -Glc-1-P) as the barium salt . When silver dibenzyl phosphate is used, the product is the β-phosphate barium salt .…”

Recent Progress in the Synthesis of Glycosyl Phosphate Derivatives

“…Nucleophilic substitution of sugar derivatives having an anomeric leaving group (e.g., glycosyl halides) with phosphates is one of the conventional methods used for synthesizing glycosyl phosphates (39,40). In addition to glycosyl halides, glycosyl imidates (41), 1,2-anhydrosugars 22 ( Fig.…”