6-O-acetylglucal → 3-O-methoxyacetyl-6-O-acetylglucal

HRID 1440003Notes

Reaction equation

HRID 1440003 reaction equation
[C:1]([O:4][CH2:5][C@H:6]1[O:11][CH:10]=[CH:9][C@@H:8]([OH:12])[C@@H:7]1[OH:13])(=[O:3])[CH3:2].[CH3:14][O:15][CH2:16][C:17](OC=C)=[O:18]>C(COC)OC>[CH3:14][O:15][CH2:16][C:17]([O:12][C@H:8]1[C@H:7]([OH:13])[C@@H:6]([CH2:5][O:4][C:1](=[O:3])[CH3:2])[O:11][CH:10]=[CH:9]1)=[O:18]

Participants

4

Reactant 2

HCID 100476776-O-acetylglucalHCID 14541961Vinyl methoxyacetate

Product 1

HCID 145419643-O-methoxyacetyl-6-O-acetylglucalYield 93.8%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

325 mg (1.73 mmol) of 6-O-acetylglucal are dissolved in 1 ml of dimethoxyethane, 1 ml of vinyl methoxyacetate and 325 mg of lipase Fp (Pseudomonas fluorescens, Amano) are added, and the mixture is stirred at room tempera-tufa for 51/2hours. Filtering off the enzyme and flash chromatography on silica gel (ethyl acetate/hexane 1:2) result in 422 mg (1.62 mmol, 93.8% yield) of the desired 3-O-methoxyacetyl-6-O-acetylglucal.

Workup

  1. filtrationFiltering off the enzyme and flash chromatography on silica gel (ethyl acetate/hexane 1:2)

Sources & evidence

ORD record
ord-a3eb1faa9d8d4dc08ed85d59708bdb7d
Source dataset
uspto-grants-1996_03
Patent number
US05496930

Reaction notes

Loading…