Methanol → 2,3-O-Isopropylidene-D-erythrofuranose

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Reaction Steps

The reduction of 2,3-O-isopropylidene-D-erythronolactone (2) was performed using a modified version of Cohen's procedure (see: Cohen, N.; et al J. Am. Chem. Soc. 1983, 105, 3661-3672). Diisobutylaluminum hydride (101 mL of a 1.5 M soln. in toluene, 152 mmol) was added in a dropwise fashion via an addition funnel to a cold (-78° C.) solution of 2,3-O-isopropylidene-D-erythronolactone (2) (see: Cohen, N.; et al in Organic Synthesis, Collective Vol, IV; J. P. Freeman, Ed.; Wiley, N.Y., 1990; pp 297-301) (20.0 g, 126 mmol) in CH2Cl2 (360 mL). After 2 h, methanol (20 mL) was added, followed by brine (10 mL). After warming to room temperature, the mixture was diluted with ether (500 mL) and MgSO4 (150 g) was added. After stirring vigorously for 4 h, the mixture was filtered with suction through a sintered glass funnel, and the filter cake was washed with ether (100 mL). The filtrate was concentrated to give 17.0 g (84%) of crude 2,3 -O-isopropylidene-D-erythrose as a pale yellow oil that was used without further purification.

Provenance & Evidence