AN IMPROVED SYNTHESIS OF DIHYDROXYACETONE PHOSPHATE

被引：55

作者：

PEDERSON, RL ^{[1
]}

ESKER, J ^{[1
]}

WONG, CH ^{[1
]}

机构：

[1] Scripps Res Inst, RES INST, DEPT CHEM, LA JOLLA, CA 92037 USA

来源：

TETRAHEDRON | 1991年 / 47卷 / 14-15期

关键词：

D O I：

10.1016/S0040-4020(01)81796-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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 H2O2 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.

引用

页码：2643 / 2648

页数：6