Sodium Acetate → HCID 69732883, compound

HRID 1760891Notes

Reaction equation

HRID 1760891 reaction equation
[C:1]([O:4][C@H:5]1[C@H:10]([O:11]C(=O)C)[C@@H:9]([CH2:15][O:16][C:17](=[O:19])[CH3:18])[O:8][CH2:7][C:6]1=[O:20])(=[O:3])[CH3:2].CC([O-])=O.[Na+]>CC(C)=O>[C:1]([O:4][C:5]1[C:6](=[O:20])[CH2:7][O:8][C@H:9]([CH2:15][O:16][C:17](=[O:19])[CH3:18])[C:10]=1[OH:11])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 517045Sodium AcetateHCID 69732337HCID 69732337, compound

Product 1

HCID 69732883HCID 69732883, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

[Litt=S. Andersen et al. J. Carbohydrate Chemistry, 17 (1998) 1027-1035, P. Jarglis and F. W. Lichtenthaler. Angew. Chem. 94 (1982) 140-141 with a benzoylated analog]. To a solution of 3,4,6-tri-O-acetyl-1,5-anhydro-D-fructose (3) (2.21 g, 7.67 mmol) in dry acetone (77 mL), anhydrous NaOAc (2.2 g) was added and the reaction mixture was stirred for 3 h. The salts were filtered off and washed with acetone. The filtrate was concentrated and purified by column chromatography (30 g silica, eluted with hexane-EtOAc. 2:1) to give 4 as a syrup (1.56 g, 89%): 1H NMR (CDCl3 at 7.27, 300 MHz) δ 2.12 (s, 3H, OCOCH3), 2.26 (s, 3H, OCOCH3), 4.24 (dd, J=4.0 and 12.0, 1H, H-6), 4.25 (dd, J=2.0 and 16.5, 1H. H-1), 4.42 (dd, J=6.0 and 12.0, 1H, H-6′), 4.46 (d, J=16.5, 1H, H-1′), 4.80 (dddd, J=2.0, 2.0, 4.0 and 6.0, 1H, H-5), 6.59 (d, J=2.0, 1H, H-4). 13C NMR (CDCl3 at 77.0, 50.3 MHz) δ 20.3-20.7 (2×OCOCH3), 64.4 (C-6), 71.4 (C-1), 72.6 (C-5), 132.8 (C-4), 143.8 (C-3), 168.1-170.7 (2×OCOCH3), 187.7 (C-2)

Workup

  1. filtrationThe salts were filtered off
  2. washwashed with acetone
  3. concentrationThe filtrate was concentrated
  4. custompurified by column chromatography (30 g silica, eluted with hexane-EtOAc. 2:1)

Sources & evidence

ORD record
ord-4ec1697872f14f0cb6438544555239b3
Source dataset
uspto-grants-2005_01
Patent number
US06846505B2

Reaction notes

Loading…