Vinyl Acetate → HCID 131719285, compound

HRID 1439993Notes

Reaction equation

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

Participants

Reactant 2

HCID 7904Vinyl Acetate

HCID 131719286HCID 131719286, compound

Product 1

HCID 131719285HCID 131719285, compoundYield 85%

Procedure

1.0 g (4 mmol) of 6-O-tert.butyldimethylsilyl-glucal in 5-10 ml of vinyl acetate is stirred with 1.0 g of lipase from Pseudomonas spec. at room temperature for 3-4 hours. Filtration, concentration and chromatography (SiO2, ether/hexane 1:3) yields the desired 3-O-acetyl-6-O-tert.-butyldimethylsilyl-glucal in approximately 85% yield (0.98-1.0 g).

Workup

filtrationFiltration, concentration and chromatography (SiO2, ether/hexane 1:3)

Sources & evidence

ORD record: ord-c623f566b486415e85e88c6cf5132d88
Source dataset: uspto-grants-1996_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05496930

Reaction notes

Loading…