HCID 131719288, compound → HCID 131719287, compound

HRID 1439994Notes

Reaction equation

HRID 1439994 reaction equation
C([O:4][C@H:5]1[C@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@@H:9]([CH2:15][O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[O:8][C:7]([SiH:21]([CH3:23])[CH3:22])=[CH:6]1)(=O)C>P([O-])([O-])([O-])=O.[K+].[K+].[K+]>[C:12]([O:11][C@@H:10]1[C@@H:9]([CH2:15][O:16][C:17]([CH3:18])([CH3:19])[CH3:20])[O:8][C:7]([SiH:21]([CH3:22])[CH3:23])=[CH:6][C@H:5]1[OH:4])(=[O:14])[CH3:13]

Participants

3

Reactant 1

HCID 131719288HCID 131719288, compound

Product 1

HCID 131719287HCID 131719287, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 62657Potassium Phosphate, TribasicSolvent

Procedure

1.03 g (3 mmol) of 3,4-di-O-acetyl-6-O-tert.butyldimethylsilyl-glucal in 10 ml of 0.1M potassium phosphate buffer (pH=7) are stirred with 0.5-1.0 g of lipase P or lipase Fp (Amano), immobilized on SiO2, at room temperature. After the reaction is complete (5-8 h), the immobilized reusable enzyme is separated off. The desired 4-O-acetyl-6-O-tert.butyldimethylsilyl-glucal is obtained either by extraction of the aqueous solution with chloroform or ethyl acetate or after freeze-drying and subsequent chromatography on silica gel (ether/hexane 1:2) in 82% yield.

Workup

  1. customimmobilized on SiO2, at room temperature
  2. custom(5-8 h)
  3. customthe immobilized reusable enzyme is separated off

Sources & evidence

ORD record
ord-5d9d5883fcec419c85dfd8797cfe4043
Source dataset
uspto-grants-1996_03
Patent number
US05496930

Reaction notes

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