Synthesis of All Diastereomers of the 2-Deoxypentoses and the 2,6-Dideoxyhexoses from 2-Phenyl-1,3-dioxan-5-one Hydrate

Autor: Ulven, Trond, Carlsen, Per H. J.
Zdroj: European Journal of Organic Chemistry; September 2001, Vol. 2001 Issue: 17 p3367-3374, 8p
Abstrakt: All diastereomers of the 2-deoxypentoses and the 2,6-dideoxyhexoses were synthesized from 2-phenyl-1,3-dioxan-5-one hydrate (1), by alkylation via the RAMP-hydrazone (2). Some of the diastereomers were synthesized in the racemic form via the dimethylhydrazone (28). The 2-deoxypentoses were synthesized by alkylation with allyl bromide, followed by stereoselective reduction, ozonolysis, and deprotection. The 2,6-dideoxypentoses were synthesized by dialkylation with allyl bromide and methyl iodide.
Databáze: Supplemental Index