Vinyl phenoxyacetate → 6-O-benzoyl-3-O-phenoxyacetylglucal

HRID 1440004Notes

Reaction equation

HRID 1440004 reaction equation
[C:1]([O:9][CH2:10][C@H:11]1[O:16][CH:15]=[CH:14][C@@H:13]([OH:17])[C@@H:12]1[OH:18])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O:19]([CH2:26][C:27](OC=C)=[O:28])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C(COC)OC>[C:1]([O:9][CH2:10][C@H:11]1[O:16][CH:15]=[CH:14][C@@H:13]([O:17][C:27](=[O:28])[CH2:26][O:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C@@H:12]1[OH:18])(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 10954083Vinyl phenoxyacetateHCID 143081056-O-Benzoyl-D-glucal

Product 1

HCID 145419766-O-benzoyl-3-O-phenoxyacetylglucalYield 88%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

226 mg (0.90 mmol) of 6-O-benzoylglucal are dissolved in 1 ml of dimethoxyethane and stirred with 1 ml of vinyl phenoxyacetate and 220 mg of lipase Fp at room temperature for 3 hours. Filtration and flash chromatography (silica gel; hexane and ether/hexane 1:1) result in 6-O-benzoyl-3-O-phenoxyacetylglucal in 88% yield (304.5 mg, 0.79 mmol).

Workup

  1. filtrationFiltration and flash chromatography (silica gel; hexane and ether/hexane 1:1)
  2. customresult in 6-O-benzoyl-3-O-phenoxyacetylglucal in 88% yield (304.5 mg, 0.79 mmol)

Sources & evidence

ORD record
ord-d8f53c3ccefd406481e0b2518d0903af
Source dataset
uspto-grants-1996_03
Patent number
US05496930

Reaction notes

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