Ethyl Acetate → 6-O-acetylglucal

HRID 1439987Notes

Reaction equation

HRID 1439987 reaction equation
[O:1]1[C@H:8]([CH2:9][OH:10])[C@@H:6]([OH:7])[C@H:4]([OH:5])[CH:3]=[CH:2]1.[C:11](OCC)(=[O:13])[CH3:12]>C(OC=C)(=O)C>[C:11]([O:10][CH2:9][C@H:8]1[O:1][CH:2]=[CH:3][C@@H:4]([OH:5])[C@@H:6]1[OH:7])(=[O:13])[CH3:12]

Participants

4

Reactant 2

HCID 8857Ethyl AcetateHCID 2734736D-(+)-Glucal

Product 1

HCID 100476776-O-acetylglucalYield 85%

Reagents, catalysts & solvents 1

HCID 7904Vinyl AcetateSolvent

Procedure

1.022 g (7 mmol) of glucal are taken up in 2 ml of ethyl acetate and 30 ml of vinyl acetate, 400 mg of lipase from Candida cylindracea lipase OF (Meito Sangyo Co. Ltd.) are added, and the mixture is stirred at room temperature overnight. After the reusable enzyme has been separated off, and subsequent chromatography or crystallization, 1.12-1.25 g of 6-O-acetylglucal (85-95% yield) are obtained.

Workup

  1. customAfter the reusable enzyme has been separated off

Sources & evidence

ORD record
ord-622e017256974e258a44c833953015fa
Source dataset
uspto-grants-1996_03
Patent number
US05496930

Reaction notes

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