Vinyl chloroacetate → 6-O-benzoyl-3-O-chloroacetylglucal

HRID 1439999Notes

Reaction equation

HRID 1439999 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.[Cl:19][CH2:20][C:21](OC=C)=[O:22]>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:21](=[O:22])[CH2:20][Cl:19])[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 82156Vinyl chloroacetateHCID 143081056-O-Benzoyl-D-glucal

Product 1

HCID 143081116-O-benzoyl-3-O-chloroacetylglucalYield 82%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

1.0 g (4 mmol) of 6-O-benzoylglucal is dissolved in 2-5 ml of dimethoxyethane and 10-15 ml of vinyl chloroacetate and stirred with 1 g of lipase P (Amano) for 1-2 h. Filtering off the enzyme and chromatography on silica gel (ether/hexane 1:1) yield 6-O-benzoyl-3-O-chloroacetylglucal in 82-87% yield.

Workup

  1. filtrationFiltering off the enzyme and chromatography on silica gel (ether/hexane 1:1)

Sources & evidence

ORD record
ord-3d173144e76245a0a9cb1ef22c454d73
Source dataset
uspto-grants-1996_03
Patent number
US05496930

Reaction notes

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