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 448668Notes

Reaction equation

HRID 448668 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-325e74754bb041eaa601b7d704aa95e3
Source dataset
uspto-grants-2013_07
Patent number
US08481712B2

Reaction notes

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