Acetic Acid → HCID 22865223, compound

HRID 2395087Notes

Reaction equation

HRID 2395087 reaction equation
C([O:4][C@H:5]1[O:28][C@H:27]([CH2:29][O:30][C:31](=[O:38])[C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH2:26][C@H:16]([O:17][C:18](=[O:25])[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C@H:6]1[O:7][C:8](=[O:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)(=O)C.[BrH:39].C(O)(=O)C>ClCCl.C(OCC)(=O)C>[Br:39][C@@:5]1([O:28][C@H:27]([CH2:29][O:30][C:31](=[O:38])[C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH2:26][C@H:16]([O:17][C:18](=[O:25])[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C@H:6]1[O:7][C:8](=[O:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[OH:4]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 54495207HCID 54495207, compound

Product 1

HCID 22865223HCID 22865223, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 1-O-acetyl-2,3,6-tri-O-benzoyl-4-deoxy-α-D-glucopyranose (0.137 g, 0.29 mmol) in 3.0 mL of dry dichloromethane at 0° C. was added 30% hydrogen bromide in acetic acid (0.07 mL, 0.33 mmol). The solution was stirred under argon at room temperature for 4 hours, diluted with ethyl acetate (100 mL) and extracted with a saturated solution of sodium bicarbonate. The organic layer was washed with a saturated solution of sodium chloride, dried over anhydrous sodium sulfate and evaporated under reduced pressure to yield the target compound as a colorless oil which solidified upon standing. Crystallization from ether and petroleum ether gave the target compound as white crystals (0.15 g, 100%).

Workup

  1. extractionextracted with a saturated solution of sodium bicarbonate
  2. washThe organic layer was washed with a saturated solution of sodium chloride
  3. dry with materialdried over anhydrous sodium sulfate
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-59d9ec7ea5e94144bd132977c9ed9884
Source dataset
uspto-grants-1998_09
Patent number
US05811512

Reaction notes

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