Phosphate migration in some phosphate monoesters and diesters of methyl α-d-mannopyranoside

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

“…149 The reaction between the acetylated mannosyl phosphate 1 and the 6-OH derivative 2 in pyridine in the presence of DCC (Scheme 2) provided the protected phosphodiester 3, which was deacetylated without purification by adding aq NaOH. The (1!6)-linked mannosyl phosphomannoside 4 was isolated by precipitation in 62% yield.…”

Binding Evaluation of Pradimicins for Oligomannose Motifs from Fungal Mannans

“…15 After deacetylation, the benzyl groups of the resulting phosphate 17 were removed to give 2. 16 The synthesis of α-1,6-linked trimannose motif 3 was initiated with the preparation of glycosyl donors 19 and 20 from thiomannoside 18 17 (Scheme 2). Acetylated donor 19 was initially coupled with 16, and the resulting dimannose 21 18 was then glycosylated with the methylated donor 20.…”

“…The spectroscopic data of 2 was perfectly identical to the reported values. 16 Synthesis of α-1,6-Linked Trimannose Motif 3. To a solution of 18 17 (2.0 g, 4.17 mmol) in pyridine (3.4 mL) was added Ac 2 O (1.9 mL) at 4°C.…”

Recent Progress in the Synthesis of Glycosyl Phosphate Derivatives

“…Moreover, the active intermediate 11 is prone to decomposition via an elimination and/or nucleophilic substitution at the anomeric position owing to the leaving ability of the anomeric phosphate group enhanced by the activation. The phosphodiester method using glycosyl phosphate monoesters gives the desired products in better yields than the phosphotriester method; however, the yields drop significantly where more sterically hindered secondary hydroxy groups are involved in the condensation reactions (27,28).…”