2-Deoxyribose, D- → 2-Deoxy-D-ribitol

HRID 452965Notes

Reaction equation

HRID 452965 reaction equation
[OH:1][C@H:2]([C@H:6]([OH:9])[CH2:7][OH:8])[CH2:3][CH:4]=[O:5].[H][H]>[Ni].O>[CH2:7]([OH:8])[C@@H:6]([OH:9])[C@@H:2]([OH:1])[CH2:3][CH2:4][OH:5]

Participants

5

Reactant 2

HCID 54600052-Deoxyribose, D-HCID 178418361HCID 178418361, compound

Product 1

HCID 107967912-Deoxy-D-ribitolYield 100.8%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 962WaterSolvent2×

Procedure

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 SS reactor. The mixture was stirred for 1.5 hr at 70° C. under 800 psi of hydrogen. 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)+.

Workup

  1. filtrationThe mixture was filtered through a nylon membrane
  2. washthe reactor was rinsed with water
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-fba31ef750644e198131fc170fd263c0
Source dataset
uspto-grants-2013_07
Patent number
US08492371B2

Reaction notes

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