Vinyl Acetate → HCID 11806454, compound

HRID 1439991Notes

Reaction equation

HRID 1439991 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](OC=C)(=[O:13])[CH3:12].[C:17](OCC)(=[O:19])[CH3:18]>>[C:11]([O:5][C@H:4]1[C@H:6]([OH:7])[C@@H:8]([CH2:9][O:10][C:17](=[O:19])[CH3:18])[O:1][CH:2]=[CH:3]1)(=[O:13])[CH3:12]

Participants

4

Reactant 3

HCID 7904Vinyl AcetateHCID 8857Ethyl AcetateHCID 2734736D-(+)-Glucal

Product 1

HCID 11806454HCID 11806454, compoundYield 90%

Procedure

7.3 g (50 mmol) of glucal are taken up in 50 ml of ethyl acetate and 150 ml of vinyl acetate and stirred at room temperature with 2 g of lipase from Pseudomonas spec. (Lipase P, from Amano Pharmaceutical Co., Ltd., Nagoya, Japan). After the reaction is complete (TLC check, about 48 h) the reusable enzyme is filtered off, and the solvent is evaporated, The 3,6-di-O-acetylglucal which results in more than 90% yield can be used without further purification for synthetic purposes.

Workup

  1. custom(TLC check, about 48 h)
  2. filtrationis filtered off
  3. customthe solvent is evaporated

Sources & evidence

ORD record
ord-a601e0cfc5f44961b8429c8f7a75d78c
Source dataset
uspto-grants-1996_03
Patent number
US05496930

Reaction notes

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