1,3,2-DIOXATHIANE 2,2-DIOXIDE

Uses

1,3,2-Dioxathiane 2,2-Dioxide is a reagent used in the synthesis of deoxy salacinols via coupling reaction.

General Description

Bacillus sp. CCZU11-1 catalyzed biotransformation of 1,3-propanediol cyclic sulfate (1,3-PDS) and its derivatives has been proposed. It can undergo biocatalyzed transformation to diols by Rhodococcus sp.

Flammability and Explosibility

Not classified

Synthesis

1,2-Diol/1,3-diol (50 mmol, 1.0 eq.) was dissolved in CH2Cl2 (30 mL) and the solution was cooled to 0C. A solution of SOCl2 (65 mmol, 1.3 eq.) in CH2Cl2 (20 mL) was added via a charging funnel over 1 hr. The reaction mixture was heated to reflux for 1 h and then cooled to room temperature. H2O (50 mL) was added to the reaction mixture, the layers were separated and the organic layer was washed with H2O (50 ml x 2) and brine (30 mL), dried (Na2SO4), filtered, and the solvent evaporated in vacuum. The unpurified sulfite was dissolved in CH3CN/CCl4 (1:1) (100 mL). The solution was cooled to 0C. Pre-cooled H2O (100 mL) was added to the mixture. A portion of solid NaIO4 (100 mmol, 2.0 eq.) and RuCl3.3H2O (500 mol, 0.5 mol%) were added. The reaction mixture was stirred vigorously for 1 hour. The phases were separated and the aqueous layer was extracted with ethyl acetate (300 mL). The combined organic layers were washed with brine, dried over Na2SO4, and concentrated under vacuum to a crude product. Purify by column chromatography (eluent: cyclohexane/EtOAc). The combined organic layers were washed with brine, dried with Na2SO4 and concentrated under vacuum to give the crude expected product, which was purified by column chromatography to give the title compound 1,3,2-dioxathiane-2,2-dioxide.