Ethyl Acetate → HCID 131719283, compound

HRID 1439988Notes

Reaction equation

HRID 1439988 reaction equation
[C:1]([O:5][C@@H:6]1[C@@H:11]([CH2:12][OH:13])[O:10][C:9]([SiH:14]([CH3:16])[CH3:15])=[CH:8][C@H:7]1[OH:17])([CH3:4])([CH3:3])[CH3:2].[C:18](OCC)(=[O:20])[CH3:19]>C(OC=C)(=O)C>[C:18]([O:13][CH2:12][C@H:11]1[O:10][C:9]([SiH:14]([CH3:15])[CH3:16])=[CH:8][C@@H:7]([OH:17])[C@@H:6]1[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])(=[O:20])[CH3:19]

Participants

4

Reactant 2

HCID 8857Ethyl AcetateHCID 131719284HCID 131719284, compound

Product 1

HCID 131719283HCID 131719283, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 7904Vinyl AcetateSolvent

Procedure

1.09 g (5 mmol) of 4-O-tert.-butyldimethylsilyl-glucal are taken up in 10-20 ml of ethyl acetate and 50-80 ml of vinyl acetate, and 1.0 g of lipase from Candida cylindracea (Sigma) is added. After stirring at room temperature for 20-24 hours, the reusable enzyme is filtered off, and the solution is concentrated in vacuo. Subsequent simple filtration through a silica gel column in ether/hexane (~1:1 v:v) yields 1.1-1.2 g of 6-O-acetyl-4-O-tert.-butyldimethylsilyl-glucal (85-90% yield).

Workup

  1. filtrationthe reusable enzyme is filtered off
  2. concentrationthe solution is concentrated in vacuo
  3. filtrationSubsequent simple filtration through a silica gel column in ether/hexane (~1:1 v:v)

Sources & evidence

ORD record
ord-2d4f5fdb7c3c4cc9a1eb06e999aeea3a
Source dataset
uspto-grants-1996_03
Patent number
US05496930

Reaction notes

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