The synthesis of d-glyceraldehyde- 3,3-d2 3-phosphate

Abstract

The synthesis of d-glyceraldehyde- 3,3-d 2 3-phosphate starting from 2- O-benzyl- d-arabinose was accomplished by a route that involved the reduction of 2- O-benzyl- d-arabinono-1,4-lactone by sodium borodeuteride. The resulting 2- O-benzyl- d-arabinitol- 1,1-d 2 was cleaved with sodium metaperiodate to yield 2-O-benzyl-3- O-formyl- d-glyceraldehyde- 3,3-d 2, which was converted into the corresponding diethyl dithioacetal. After removal of the formyl group, the dithioacetal was converted into 2- O-benzyl- d-glyceraldehyde- 3,3-d 2 dimethyl acetal. Phosphorylation of the latter with diphenyl phosphorochloridate and removal of the protecting groups afforded d-glyceraldehyde- 3,3-d 2 3-phosphate. The reaction sequence is also suitable for the synthesis of d-glyceraldehyde- 3-t 3-phosphate. Use of d-glyceraldehyde- 3,3-d 2 3-phosphate for the synthesis of d-fructose- 6,6-d 2 1,6-diphosphate is also described.