Vinyl benzoate → 6-O-Benzoyl-D-glucal

HRID 1440001Notes

Reaction equation

HRID 1440001 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.[C:11](OC=C)(=[O:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>O1CCCC1>[C:11]([O:10][CH2:9][C@H:8]1[O:1][CH:2]=[CH:3][C@@H:4]([OH:5])[C@@H:6]1[OH:7])(=[O:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 13037Vinyl benzoateHCID 2734736D-(+)-Glucal

Product 1

HCID 143081056-O-Benzoyl-D-glucal

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1.0 g (6.85 mmol) of glucal is taken up in 1.5-2.0 ml of tetrahydrofuran and 3-5 ml of vinyl benzoate and stirred with 1 g of lipase from Candida cylindracea (Amano AY-20) at room temperature for 6 h. Filtering off the enzyme, concentration of the solution in vacuo, taking up the residue in ethyl acetate and extracting it with aqueous NaHCO3 solution, and subsequent chromatography on silica gel (ethyl acetate/hexane 1:1) result in 1.20 g (70%) of the desired 6-O-benzoylglucal.

Workup

  1. filtrationFiltering off the enzyme, concentration of the solution in vacuo
  2. extractionextracting it with aqueous NaHCO3 solution, and subsequent chromatography on silica gel (ethyl acetate/hexane 1:1)
  3. customresult in 1.20 g (70%) of the desired 6-O-benzoylglucal

Sources & evidence

ORD record
ord-789f67559fe548fd9ced8fbbfb8c847d
Source dataset
uspto-grants-1996_03
Patent number
US05496930

Reaction notes

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