Acetone → HCID 54047185, compound

HRID 1461463Notes

Reaction equation

HRID 1461463 reaction equation
[CH2:1]([O:8][C@H:9]1[C@H:18]([O:19][C:20](=[O:22])[CH3:21])[C@@H:17]([CH2:23][OH:24])[O:16][CH:11]([O:12][C:13](=[O:15])[CH3:14])[C@@H:10]1[O:25][C:26](=[O:28])[CH3:27])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(C)=[O:31]>S(=O)(=O)(O)O.[O-2].[O-2].[O-2].[Cr+6]>[CH2:1]([O:8][C@H:9]1[C@H:18]([O:19][C:20](=[O:22])[CH3:21])[C@@H:17]([C:23]([OH:31])=[O:24])[O:16][CH:11]([O:12][C:13](=[O:15])[CH3:14])[C@@H:10]1[O:25][C:26](=[O:28])[CH3:27])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 180AcetoneHCID 54051596HCID 54051596, compound

Product 1

HCID 54047185HCID 54047185, compoundYield 54%

Reagents, catalysts & solvents 2

HCID 10219390chromium (VI) trioxideCatalystHCID 1118Sulfuric AcidSolvent

Procedure

A solution of crude 17 in the minimum amount of dichloromethane was stirred at room temperature with aqueous 80% acetic acid (100 mL) until TLC demonstrated the disappearance of 17. Water was then added with stirring; the solid was removed and the filtrate was concentrated. The crude 3-O-benzyl-1,2,4-tri-O-acetyl-D-glucopyranose (18) was thus obtained; 1H NMR data: 60:40 mixture of anomers 6.32 (d, 1 H, alpha-H), 5.64 (d, 1 H, beta-H). A solution of the crude residue 18 in acetone was cooled to -5° C. and a solution of chromium trioxide in 3.5M sulfuric acid was added dropwise with stirring. The mixture was allowed to attain room temperature, and, after 5 hours at room temperature, was poured into ice-cold water and extracted with chloroform. The extract was washed with water and concentrated, and a solution of the crude methyl ester of 3-O-benzyl-1,2,4-tri-O-acetyl-D-glucopyranosuronic acid (19) in ether was esterified with ethereal diazomethane. The product was eluted from a column of silica gel with chloroform-ethyl acetate (20:10) to give 19 (54%). 1H NMR date: mixture of anomers alpha:beta=60:40; 7.23-7.36 (m, 5 H, arom.), 6.38 (d, 1 H, alpha-H), 5.69 (d, 1 H, beta-H), 3.72 (s, 3 H, alpha-COOMe), 3.71 (s, 3 H, beta-COOMe), 1.96-2.16 (9 H, Ac).

Workup

  1. addition1H NMR data: 60:40 mixture of anomers 6.32 (d, 1 H, alpha-H), 5.64 (d, 1 H, beta-H)
  2. customto attain room temperature
  3. additionwas poured into ice-cold water
  4. extractionextracted with chloroform
  5. washThe extract was washed with water
  6. concentrationconcentrated
  7. washThe product was eluted from a column of silica gel with chloroform-ethyl acetate (20:10)

Sources & evidence

ORD record
ord-71df10ec38de4537b77c82b3ca34fd37
Source dataset
uspto-grants-1991_12
Patent number
US05075433

Reaction notes

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