Potassium Carbonate → HCID 58786151, compound

HRID 1375968Notes

Reaction equation

HRID 1375968 reaction equation
C([SiH](CC)CC)C.[CH2:8]([O:15][C@@H:16]1[C@@H:22]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C@H:21]([O:31][CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C@@H:20]([CH2:39][O:40][CH2:41][C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[O:19][C:17]1([C:48]1[CH:53]=[C:52]([CH3:54])[CH:51]=[CH:50][C:49]=1[O:55][CH2:56][CH3:57])O)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(=O)([O-])[O-].[K+].[K+]>>[CH2:8]([O:15][C@@H:16]1[C@@H:22]([O:23][CH2:24][C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[C@H:21]([O:31][CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C@@H:20]([CH2:39][O:40][CH2:41][C:42]2[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=2)[O:19][C@H:17]1[C:48]1[CH:53]=[C:52]([CH3:54])[CH:51]=[CH:50][C:49]=1[O:55][CH2:56][CH3:57])[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

4

Reactant 3

HCID 11430Potassium CarbonateHCID 12052TriethylsilaneHCID 58786166HCID 58786166, compound

Product 1

HCID 58786151HCID 58786151, compoundYield 99.5%

Procedure

Boron trifluoride-diethyl ether complex (0.6 ml) and triethylsilane (1.7 ml) were added dropwise to a solution of 2,3,4,6-tetra-O-benzyl-1-C-(2-ethoxy-5-methylphenyl)-D-glucopyranose (3.5 g) at −50° C. and the mixture was stirred for two hours. Saturated aqueous solution of potassium carbonate was added to the reaction mixture and the mixture was extracted with chloroform. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated. The residue was purified by silica gel column chromatography (hexane-ethyl acetate) to obtain (1S)-1,5-anhydro-2,3,4,6-tetra-O-benzyl-1-(2-ethoxy-5-methylphenyl)-D-glucitol (3.4 g).

Workup

  1. extractionthe mixture was extracted with chloroform
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationAfter filtration
  5. concentrationthe filtrate was concentrated
  6. customThe residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-1a44c6cd78834a85976a814b42185d94
Source dataset
uspto-grants-2007_01
Patent number
US07169761B2

Reaction notes

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