Potassium Carbonate → HCID 58786151、化合物

HRID 1375968ノート

反応式

HRID 1375968 の反応式
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

参加物

4

反応物 3

HCID 11430Potassium CarbonateHCID 12052TriethylsilaneHCID 58786166HCID 58786166、化合物

生成物 1

HCID 58786151HCID 58786151、化合物収率 99.5%

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-1a44c6cd78834a85976a814b42185d94
出典データセット
uspto-grants-2007_01
特許番号
US07169761B2

反応ノート

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