Acetic Acid → HCID 54051596, compound

HRID 1461462Notes

Reaction equation

HRID 1461462 reaction equation
ClCCl.C(O)(=O)C.[CH2:8]([O:15][C@H:16]1[C@H:25]([O:26][C:27](=[O:29])[CH3:28])[C@@H:24]([CH2:30][O:31]C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[O:23][CH:18]([O:19][C:20](=[O:22])[CH3:21])[C@@H:17]1[O:51][C:52](=[O:54])[CH3:53])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>O>[CH2:8]([O:15][C@H:16]1[C@H:25]([O:26][C:27](=[O:29])[CH3:28])[C@@H:24]([CH2:30][OH:31])[O:23][CH:18]([O:19][C:20](=[O:22])[CH3:21])[C@@H:17]1[O:51][C:52](=[O:54])[CH3:53])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 6344DichloromethaneHCID 22841875HCID 22841875, compound

Product 1

HCID 54051596HCID 54051596, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

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. customthe solid was removed
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-639003842a6945169ccd74077488d26c
Source dataset
uspto-grants-1991_12
Patent number
US05075433

Reaction notes

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