Potassium Carbonate → HCID 58786211, compound

HRID 1375990Notes

Reaction equation

HRID 1375990 reaction equation
C([SiH](C(C)C)C(C)C)(C)C.[CH2:11]([O:18][C@@H:19]1[C@@H:25]([O:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C@H:24]([O:34][CH2:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[C@@H:23]([CH2:42][O:43][CH2:44][C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)[O:22][C:20]1([C:51]1[CH:56]=[CH:55][CH:54]=[C:53]([CH2:57][C:58]2[C:67]3[C:61]([CH:62]=[CH:63][CH:64]=[CH:65][CH:66]=3)=[C:60]([CH3:68])[CH:59]=2)[CH:52]=1)O)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH2:11]([O:18][C@@H:19]1[C@@H:25]([O:26][CH2:27][C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[C@H:24]([O:34][CH2:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[C@@H:23]([CH2:42][O:43][CH2:44][C:45]2[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=2)[O:22][C@H:20]1[C:51]1[CH:56]=[CH:55][CH:54]=[C:53]([CH2:57][C:58]2[C:67]3[C:61]([CH:62]=[CH:63][CH:64]=[CH:65][CH:66]=3)=[C:60]([CH3:68])[CH:59]=2)[CH:52]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 138754Silane, tris(1-methylethyl)-HCID 69381461HCID 69381461, compound

Product 1

HCID 58786211HCID 58786211, compoundYield 65.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Boron trifluoride-diethyl ether complex (0.39 ml) and triisopropylsilane (1.23 ml) were added dropwise to a solution of 2,3,4,6-tetra-O-benzyl-1-C-[3-[(3-methylazulen-1-yl) methyl]phenyl]-D-glucopyranose (2.3 g) in acetonitrile (40 ml) at −40° 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 ethyl acetate. 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 (n-hexane-ethyl acetate) to obtain (1S)-1,5-anhydro-2,3,4,6-tetra-O-benzyl-1-[3-[(3-methyl azulen-1-yl)methyl]phenyl]-D-glucitol (1.47 g).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  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 (n-hexane-ethyl acetate)

Sources & evidence

ORD record
ord-57568bb396d44d1a91761c92a22d4813
Source dataset
uspto-grants-2007_01
Patent number
US07169761B2

Reaction notes

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