Richard L. Pederson, J. Esker, Chi‐Huey Wong
1991
Citations
0
Influential Citations
38
Citations
Journal
Tetrahedron
Abstract
Abstract An improved procedure has been developed for the synthesis of dihydroxyacetone phosphate (DHAP). Reaction of 2,5-diethoxy-p-dioxane-2,5-dimethanol ( 1 ) and the trivalent phosphorylating reagent dibenzyl-N,N-diethylphosphoramidite (DDP) in the presence of 1,2,4-triazole or tetrazole followed by oxidation with H 2 O 2 gave 2,5-diethoxy-p-dioxane-2,5-dimethanol-O-2 1 -O-5 1 - bis(phosphate) tetrabenzyl ester ( 2 ) in 98% yield. Compound 2 was then hydrogenated in the presence of H 2 -Pd/C to give, after neutralization, 2,5-diethoxy-p-dioxane-2,5-dimethanol-O-2 1 -O-5 1 -bis(phosphate) as a stable trisodium salt ( 3 ) in 84% yield. Treatment of 3 with Dowex 50 (H+) generates 2 equivalents of DHAP.