2-Deoxyribose, D- → 2-Deoxy-D-ribitol

Participants

Reaction Steps

Water (50 mL) and Ra—Ni, water-wet (5.03 g, 38.6 mmol) were added to (3S,4R)-3,4,5-trihydroxypentanal (25.19 g, 188 mmol) in a 300 mL stainless steel reactor. The mixture was stirred for 1.5 hr at 70° C. under 800 psi (literature 570 psi) of hydrogen. The 270 psi pressure drop was consistent with full conversion, and the DCI-MS showed only ions for the expected product. The mixture was filtered through a nylon membrane, the reactor was rinsed with water, and the filtrate was concentrated and afforded 25.8 g of the title compound. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.36-1.48 (m, 1H) 1.66-1.77 (m, 1H) 3.20-3.27 (m, 1H) 3.33 (dd, J=11.66, 6.14 Hz, 1H) 3.38-3.59 (m, 4H) 4.25-4.33 (m, 3H) 4.40 (d, J=5.22 Hz, 1H); MS (ESI) m/z 137 (M+H)+.

Provenance & Evidence