2-o-Acetyl-3,5-bis-o-(2,4-dichlorobenzyl)-1-o-methyl-alpha-d-ribofuranose → 1-Methyl-3,5-bis-O-(2,4-dichlorobenzyl)-alpha-D-ribofuranoside

HRID 1836223Notes

Reaction equation

HRID 1836223 reaction equation
C([O:4][C@@H:5]1[C@H:11]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=2[Cl:21])[C@@H:10]([CH2:22][O:23][CH2:24][C:25]2[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][C:26]=2[Cl:32])[O:9][C@@H:6]1[O:7][CH3:8])(=O)C>C([O-])([O-])=O.[K+].[K+]>[Cl:21][C:15]1[CH:16]=[C:17]([Cl:20])[CH:18]=[CH:19][C:14]=1[CH2:13][O:12][C@@H:11]1[C@@H:10]([CH2:22][O:23][CH2:24][C:25]2[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][C:26]=2[Cl:32])[O:9][C@H:6]([O:7][CH3:8])[C@@H:5]1[OH:4]

Participants

3

Reactant 1

HCID 110168142-o-Acetyl-3,5-bis-o-(2,4-dichlorobenzyl)-1-o-methyl-alpha-d-ribofuranose

Product 1

HCID 109944831-Methyl-3,5-bis-O-(2,4-dichlorobenzyl)-alpha-D-ribofuranosideYield 101.6%

Reagents, catalysts & solvents 1

HCID 11430Potassium CarbonateSolvent

Procedure

A mixture of 2-O-acetyl-3,5-bis-O-(2,4-dichlorophenylmethyl)-1-O-methyl-α-D-ribofuranose [for preparation, see: Helv. Chim. Acta 78:486 (1995)] (52.4 g, 0.10 mol) in methanolic K2CO3 (500 mL, saturated at room temperature) was stirred at room temperature for 45 min. and then concentrated under reduced pressure. The oily residue was suspended in CH2Cl2 (500 mL), washed with water (300 mL+5×200 mL) and brine (200 mL), dried (Na2SO4), filtered, and concentrated to give the title compound (49.0 g) as colorless oil, which was used without further purification in Step B below.

Workup

  1. concentrationconcentrated under reduced pressure
  2. washwashed with water (300 mL+5×200 mL) and brine (200 mL)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-eff8ad3746f6493482c3fc48b8297753
Source dataset
uspto-grants-2004_08
Patent number
US06777395B2

Reaction notes

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