Water → HCID 11806454, compound

HRID 1439992Notes

Reaction equation

[O:1]1[C@H:8]([CH2:9][OH:10])[C@@H:6](O)[C@H:4]([OH:5])[CH:3]=[CH:2]1.[OH2:11].[C:12]([O:15][C:16]([CH3:18])=C)(=[O:14])[CH3:13]>>[C:2]([O:1][C@H:8]1[C@H:9]([OH:10])[C@@H:18]([CH2:16][O:15][C:12](=[O:14])[CH3:13])[O:5][CH:4]=[CH:6]1)(=[O:11])[CH3:3]

Participants

Reactant 3

HCID 962Water

HCID 7916Isopropenyl acetate

HCID 2734736D-(+)-Glucal

Product 1

HCID 11806454HCID 11806454, compoundYield 60%

Procedure

1.02 g (7 mmol) of glucal, 0.5-0.7 ml of H2O and about 2 g of crushed molecular sieves are taken up in 25-50 ml of isopropenyl acetate, and 1 g of lipase from Pseudomonas spec. is added and the mixture is stirred at room temperature for 25-30 h. Filtration and concentration in vacuo are followed by chromatography on silica gel (ethyl acetate/hexane 2:3, v:v). 0.97-1.05 g (60-65%) of 3,6-di-O-acetylglucal are obtained.

Workup

additionis added
filtrationFiltration and concentration in vacuo

Sources & evidence

ORD record: ord-6eec91cfeaf74770a5c2911858db15d4
Source dataset: uspto-grants-1996_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05496930

Reaction notes

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