Water → HCID 86660595, compound

HRID 1808715Notes

Reaction equation

HRID 1808715 reaction equation
Br[C:2]([C@:4]([C:28](=[O:35])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)([C@:6]([C:20](=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)([C@:8]([C:12](=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)([CH2:10][OH:11])[OH:9])[OH:7])[OH:5])=[O:3].O>CC(C)=O.C(=O)([O-])[O-].[Ag+2]>[C:28]([C@@:4]([C@:6]([C:20](=[O:27])[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)([C@:8]([C:12](=[O:19])[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)([CH2:10][OH:11])[OH:9])[OH:7])([OH:5])[CH:2]=[O:3])(=[O:35])[C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

Participants

5

Reactant 2

HCID 962WaterHCID 86660594HCID 86660594, compound

Product 1

HCID 86660595HCID 86660595, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 178418647HCID 178418647, compoundCatalystHCID 180AcetoneSolvent

Procedure

Crude 1-bromo-2,3,4-tri-benzoyl-L-ribose 21 (13.3 g, 25.3 mmol) was dissolved in acetone (150 mL) and water (5 ml, 277 mmol) at 0° C. Silver carbonate (6.28 g, 22.7 mmol) was added over 5 min. The reaction was brought to room temperature after 15 min and stirred an additional 30 min. The solids were removed by filtration and washed with acetone (100 mL) and the filtrate was concentrated in vacuo. The water was removed via azeotropic distillation with ethanol and toluene and the residue was purified by silica gel flash chromatography (4:1 Hexanes:EtOAc to EtOAc) to give 22 as white solid (9.8 g, 21.2 mmol, 85%).

Workup

  1. customat 0° C
  2. customThe solids were removed by filtration
  3. washwashed with acetone (100 mL)
  4. concentrationthe filtrate was concentrated in vacuo
  5. customThe water was removed via azeotropic distillation with ethanol and toluene
  6. customthe residue was purified by silica gel flash chromatography (4:1 Hexanes:EtOAc to EtOAc)

Sources & evidence

ORD record
ord-56b0c65222134588946e39214f66707b
Source dataset
uspto-grants-2013_01
Patent number
US08361973B2

Reaction notes

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