D-(+)-Glucal → D-Galactal

HRID 1653623Notes

Reaction equation

HRID 1653623 reaction equation
[O:1]1[C@H:8]([CH2:9][OH:10])[C@@H:6]([OH:7])[C@H:4]([OH:5])[CH:3]=[CH:2]1>O>[O:1]1[C@H:8]([CH2:9][OH:10])[C@H:6]([OH:7])[C@H:4]([OH:5])[CH:3]=[CH:2]1

Participants

3

Reactant 1

HCID 2734736D-(+)-Glucal

Product 1

HCID 2734735D-GalactalYield 50%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Glycals have been examined by Lehmann et al. [Brockhaus et al., J. Carbohydr. Res., 53:21 (1977); Lehmann et al., Carbohydr. Res., 58:65 (1977); Lehmann et al., Carbohydr. Res., 58:72 (1977)] in glycosidase-mediated coupling reactions. Those investigators determined that glucal in the presence of emulsin β-glucosidase forms 2-deoxy-Gluβ1,3-glucal in up to 50 percent yield. In addition, incubation of D-galactal in the presence of glycol or water and β-galactosidase formed the corresponding glycosides via addition across the double bond. D-Glucal was reported to react similarly in the presence of β-glucosidase.

Sources & evidence

ORD record
ord-614d606c60454e9ea1e47ea3df1377db
Source dataset
uspto-grants-1995_04
Patent number
US05403726

Reaction notes

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