(4S,5S)-4-(1,3-dioxolan-2-yl)-5-(hydroxymethyl)dihydrofuran-2(3H)-one → (2S,3S)-3-[1,3]dioxolan-2-ylpentane-1,2,5-triol

HRID 896833Notes

Reaction equation

HRID 896833 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[O:7]1[CH2:11][CH2:10][O:9][CH:8]1[C@@H:12]1[C@@H:16]([CH2:17][OH:18])[O:15][C:14](=[O:19])[CH2:13]1>C1COCC1>[O:7]1[CH2:11][CH2:10][O:9][CH:8]1[C@@H:12]([CH2:13][CH2:14][OH:19])[C@H:16]([OH:15])[CH2:17][OH:18]

Participants

4

Reactant 2

HCID 11116788(4S,5S)-4-(1,3-dioxolan-2-yl)-5-(hydroxymethyl)dihydrofuran-2(3H)-oneHCID 21226445Aluminium lithium hydride

Product 1

HCID 69747925(2S,3S)-3-[1,3]dioxolan-2-ylpentane-1,2,5-triol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of lithium aluminum hydride (76 mg, 1.98 mmols) in THF (10 ml) at 0° C. was added dihydrofuranone 15 (275 mg, 1.46 mmol) in THF (30 mL) dropwise. Upon completion of the reduction after 4 hours, the reaction was quenched with a saturated aqueous sodium sulfate solution at 0° C. The solvent then was decanted and the remaining residue was washed with THF (3×), EtOAc (3×), and CHCl3 (3×). The organic extracts were combined and the solvent was removed under reduced pressure, yielding a crude (2S,3S)-3-[1,3]dioxolan-2-ylpentane-1,2,5-triol, which was immediately used in the next reaction.

Workup

  1. customthe reaction was quenched with a saturated aqueous sodium sulfate solution at 0° C
  2. customThe solvent then was decanted
  3. washthe remaining residue was washed with THF (3×), EtOAc (3×), and CHCl3 (3×)
  4. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-54c6cd1922184409b4fa207ad6d0215d
Source dataset
uspto-grants-2005_07
Patent number
US06919465B2

Reaction notes

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