Vinyl Acetate → 3-O-acetyl-6-O-benzoylglucal

HRID 1439995Notes

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.[C:19](OC=C)(=[O:21])[CH3:20]>>[C:19]([O:17][C@H:13]1[C@H:12]([OH:18])[C@@H:11]([CH2:10][O:9][C:1](=[O:8])[C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[O:16][CH:15]=[CH:14]1)(=[O:21])[CH3:20]

Participants

Reactant 2

HCID 7904Vinyl Acetate

HCID 143081056-O-Benzoyl-D-glucal

Product 1

HCID 143081143-O-acetyl-6-O-benzoylglucalYield 88%

Procedure

1.0 g (4 mmol) of 6-O-benzoylglucal is taken up in 10-20 ml of vinyl acetate and stirred with 1 g of lipase (Pseudomonas spec.) at room temperature for 5 h. Filtering off the enzyme and crystallization or chromatography on silica gel (ethyl acetate/hexane 1:1) yields 3-O-acetyl-6-O-benzoylglucal in 88-94% yield (1.03-1.10 g).

Workup

filtrationFiltering off
customthe enzyme and crystallization or chromatography on silica gel (ethyl acetate/hexane 1:1)

Sources & evidence

ORD record: ord-fc2fd86f0da8478c9789686d75e3e3c6
Source dataset: uspto-grants-1996_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05496930

Reaction notes

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