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

HRID 466902Notes

Reaction equation

HRID 466902 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 chloride

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) is treated with ethereal hydrogen chloride (0.2 g/mL, 25 mL). The mixture is stirred at room temperature during 48 h. The solvents are evaporated under reduced pressure so as to afford an oil. Flash chromatography on silica gel and elution with a graded mixture of carbon tetrachloride and ethyl acetate will afford 4-O-acetyl-2,3,6-tri-O-benzyl-α-D-galactopyranosyl chloride as an oil.

Workup

  1. customThe solvents are evaporated under reduced pressure so as
  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-f217e514001745f4b7dc858292071ffa
Source dataset
uspto-grants-1992_10
Patent number
US05157116

Reaction notes

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