(+)-2,3-O-BENZYLIDENE-D-THREITOL synthesis

Yield:58383-35-0 95.6%

Reaction Conditions:

with sodium tetrahydroborate in ethanol at 0 - 20; for 1.5 h;

Steps:

2 Example 2; (4R,5R)-4,5-dihydroxymethyl-2-phenyl-1,3-dioxolan (3d)

A solution of diethyl(4S,5S)-2-phenyl-1,3-dioxolan-4,5-dicarboxylate (2d) (30 g, 0.102 mol) in ethanol (150 ml) was added dropwise to an ice-cold solution of sodium borohydride (6.7g, 0.163 mol) in ethanol (100 ml).. Then, the admixture was stirred at room temperature for 1.5 hours.. After the solvent was removed, ethyl acetate (200 ml) was added to the admixture.. The resulting product was washed with saturated saline solution, and anhydrous magnesium sulfate was added thereto.. After filtration, the solvent was removed, to obtain 20.5 g (95. 6 % yield) of the titled compound.1H-NMR (CDCl3) δ:2.29-2.37 (2H, m), 3.74-3.91 (4H, m), 4.17 (2H, s), 6.00 (1H, s), 7.38-7.43 (3H, m), 7.46-7.51 (2H, m).

References:

EP1375465,2004,A1 Location in patent:Page 14