Water → HCID 13845546, compound

HRID 556776Notes

Reaction equation

HRID 556776 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:4]=1[C:11]1([O:41][C@H:40]([CH2:42][O:43][CH2:44][C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)[C@@H:31]([O:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[C@H:22]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C@H:13]1[O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)O.C([SiH](CC)CC)C.C(=O)([O-])[O-].[K+].[K+].O>C(#N)C>[CH2:15]([O:14][C@@H:13]1[C@@H:22]([O:23][CH2:24][C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[C@H:31]([O:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[C@@H:40]([CH2:42][O:43][CH2:44][C:45]2[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=2)[O:41][C@H:11]1[C:4]1[CH:5]=[CH:6][C:7]([O:9][CH3:10])=[CH:8][C:3]=1[O:2][CH3:1])[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 12052TriethylsilaneHCID 66765962HCID 66765962, compound

Product 1

HCID 13845546HCID 13845546, compoundYield 66.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 1-(2,4-dimethoxyphenyl)-2,3,4,6-tetra-O-benzyl-D-glucopyranose (1.7 g) and triethylsilane (0.59 g) in acetonitrile (20 mL) was added boron trifluoride diethyl ether complex (0.40 g) under ice-cooling, and the mixture was warmed to room temperature and stirred overnight. A saturated potassium carbonate aqueous solution was added to the reaction mixture, and the mixture was stirred for 30 minutes. The mixture was poured into water, and the mixture was extracted with diethyl ether. The organic layer washed with water and brine and dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=6/1) to give the title compound (1.1 g).

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred for 30 minutes
  3. extractionthe mixture was extracted with diethyl ether
  4. washThe organic layer washed with water and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was removed under reduced pressure
  7. customThe residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=6/1)

Sources & evidence

ORD record
ord-d65dbd748b394b6fae29d5162d117624
Source dataset
uspto-grants-2011_11
Patent number
US08058245B2

Reaction notes

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