Water → HCID 86660592, compound

HRID 1808713Notes

Reaction equation

HRID 1808713 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 86660593HCID 86660593, compound

Product 1

HCID 86660592HCID 86660592, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 178418647HCID 178418647, compoundCatalystHCID 180AcetoneSolvent

Procedure

Crude 1-bromo-2,3,4-tri-benzoyl-L-xylose 17 (14.1 g, 26.8 mmol) was dissolved in acetone (150 mL) and water (5 ml, 277 mmol) at 0° C. Silver carbonate (6.61 g, 24.0 mmol) was added over 5 min and 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), the filtrate was concentrated in vacuo, 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 yield 18 as white solid (9.1 g, 19.6 mmol, 74%).

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, water
  5. customwas 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-cd5f12d0c93842f19a6c4181ec73cf94
Source dataset
uspto-grants-2013_01
Patent number
US08361973B2

Reaction notes

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