Hydrochloric Acid → 4-O-acetyl-2,3,6-tri-O-benzyl-alpha-D-galactopyranosyl chloride

HRID 2372156Notes

Reaction equation

HRID 2372156 reaction equation
C(O[CH:5]1[O:30][C@H:29]([CH2:31][O:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[C@H:24]([O:25][C:26](=[O:28])[CH3:27])[C@H:15]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C@H:6]1[O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)(=O)C.[ClH:40]>CCOCC>[C:26]([O:25][C@H:24]1[C@@H:29]([CH2:31][O:32][CH2:33][C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)[O:30][C@H:5]([Cl:40])[C@H:6]([O:7][CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C@H:15]1[O:16][CH2:17][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)(=[O:28])[CH3:27]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 53796600HCID 53796600, compound

Product 1

HCID 544033654-O-acetyl-2,3,6-tri-O-benzyl-alpha-D-galactopyranosyl chlorideYield 71%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of 1,4-di-O-acetyl-2,3,6-tri-O-benzyl-D-galactopyranose (4.64 g, 8.67 mmol) in ether (10 mL) was treated with ethereal hydrogen chloride (0.2 g/mL, 25 mL). The mixture was stirred at room temperature during 48 h. The solvents were evaporated under reduced pressure to afford an oil. Flash chromatography on silica gel and elution with a graded mixture of carbon tetrachloride and ethyl acetate afforded 4-O-acetyl-2,3,6-tri-O-benzyl-α-D-galactopyranosyl chloride (3.142 g, 71%) as an oil.

Workup

  1. customThe solvents were evaporated under reduced pressure
  2. customto afford an oil
  3. washFlash chromatography on silica gel and elution
  4. additionwith a graded mixture of carbon tetrachloride and ethyl acetate

Sources & evidence

ORD record
ord-fd3b706121f64d1f970d470a91cbae85
Source dataset
uspto-grants-1992_03
Patent number
US05097023

Reaction notes

Loading…