3,5-Dichlorobenzoic acid → HCID 15108964, compound

1.28 g (10.0 mmol) of 1,6-anhydro-3,4-dideoxy-β-D-threo-hex-3-enopyranose, 5.25 g (20.0 mmol) of triphenyl phosphine, and 3.80 g (20.0 mmol) of 3,5-dichlorobenzoic acid were added to 16 ml of dry THF, and a solution obtained by dissolving 3.48 g (20.0 mmol) of diethylazodicarboxylate in 16 ml of dry THF was gradually dropped in the above mixture in a nitrogen-sealed ice-water bath. The resultant solution was stirred at room temperature for 41 hours. The solvent was distilled from the reaction solution at a reduced pressure. Triphenyl phosphine oxide as a byproduct was eliminated from the residue using a silica gel column (eluent: chloroform). The solvent was distilled from the resultant eluate at a reduced pressure, and the residue was purified using a silica gel column (hexane:ethyl acetate=6:1) to obtain 2.34 g (yield: 77.7%) of 1,6-anhydro-2-O-(3,5-dichlorobenzoyl)-3,4-dideoxy-β-D-erythro-hex-3-enopyranose. This product was recrystallized from a solvent mixture of hexane, diethyl ether, and chloroform.

1. customa solution obtained
2. additionwas gradually dropped in the above mixture in a nitrogen-
3. customsealed ice-water bath
4. distillationThe solvent was distilled from the reaction solution at a reduced pressure
5. distillationThe solvent was distilled from the resultant eluate at a reduced pressure
6. customthe residue was purified

ORD record

ord-6e8b53ee7f994c3aa5450224a3263a9a

Source dataset

uspto-grants-1995_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05457192