Acetic Anhydride → (3S,4R,5R,6S)-3,4,5-tris(benzyloxy)-6-methyltetrahydro-2H-pyran-2-one

HRID 522165Notes

Reaction equation

HRID 522165 reaction equation
C(OC(=O)C)(=O)C.[CH2:8]([O:15][C@H:16]1[C@H:21]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C@H:20]([O:30][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C@H:19]([CH3:38])[O:18][CH:17]1[OH:39])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.CCOC(C)=O>CS(C)=O>[CH2:8]([O:15][C@H:16]1[C@H:21]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C@H:20]([O:30][CH2:31][C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)[C@H:19]([CH3:38])[O:18][C:17]1=[O:39])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8857Ethyl AcetateHCID 2734155(3S,4R,5R,6S)-3,4,5-Tris(benzyloxy)-6-methyltetrahydro-2H-pyran-2-ol

Product 1

HCID 10432954(3S,4R,5R,6S)-3,4,5-tris(benzyloxy)-6-methyltetrahydro-2H-pyran-2-oneYield 62.7%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Acetic anhydride (7.40 mL, 78 mmol, commercially available from Sigma Aldrich) was added to a solution of (3S,4R,5R,6S)-3,4,5-tris(benzyloxy)-6-methyltetrahydro-2H-pyran-2-ol (1.70 g, 3.91 mmol) in DMSO (12 mL), and the resulting mixture was stirred for 24 h at P. EtOAc was added, and the mixture was washed with water (3×), dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo to give an oil. The oil was purified by silica gel chromatography (0 to 40% EtOAc/hexanes gradient) to give (3S,4R,5R,6S)-3,4,5-tris(benzyloxy)-6-methyltetrahydro-2H-pyran-2-one as a colorless oil (1.06 g, 62.6% yield). ESI (M+H) 433.1; calc for C27H28O5 432.2.

Workup

  1. washthe mixture was washed with water (3×)
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customto give an oil
  6. customThe oil was purified by silica gel chromatography (0 to 40% EtOAc/hexanes gradient)

Sources & evidence

ORD record
ord-c5f397889e5447b2b75d23cf8b4758c5
Source dataset
uspto-grants-2016_05
Patent number
US09328134B2

Reaction notes

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