Ammonium Chloride → 2,3,4,6-tetra-O-benzyl-1-[7-(4-methylbenzyl)benzo[b]thiophen-2-yl]-D-glucopyranose

HRID 15410노트

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HRID 15410 반응식
[CH3:1][C:2]1[CH:17]=[CH:16][C:5]([CH2:6][C:7]2[C:12]3[S:13][CH:14]=[CH:15][C:11]=3[CH:10]=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.C([Li])CCC.[CH2:23]([O:30][C@@H:31]1[C@@H:37]([O:38][CH2:39][C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[C@H:36]([O:46][CH2:47][C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)[C@@H:35]([CH2:54][O:55][CH2:56][C:57]2[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=2)[O:34][C:32]1=[O:33])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.[Cl-].[NH4+]>O1CCCC1>[CH2:23]([O:30][C@@H:31]1[C@@H:37]([O:38][CH2:39][C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[C@H:36]([O:46][CH2:47][C:48]2[CH:49]=[CH:50][CH:51]=[CH:52][CH:53]=2)[C@@H:35]([CH2:54][O:55][CH2:56][C:57]2[CH:58]=[CH:59][CH:60]=[CH:61][CH:62]=2)[O:34][C:32]1([C:14]1[S:13][C:12]2[C:7]([CH2:6][C:5]3[CH:4]=[CH:3][C:2]([CH3:1])=[CH:17][CH:16]=3)=[CH:8][CH:9]=[CH:10][C:11]=2[CH:15]=1)[OH:33])[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

참가 물질

6

반응물 4

HCID 25517Ammonium ChlorideHCID 10907626(3R,4S,5R,6R)-3,4,5-Tris(benzyloxy)-6-((benzyloxy)methyl)oxan-2-oneHCID 670691007-(4-Methylbenzyl)benzo[b]thiopheneHCID 178418339Butyllithium

생성물 1

HCID 687177102,3,4,6-tetra-O-benzyl-1-[7-(4-methylbenzyl)benzo[b]thiophen-2-yl]-D-glucopyranose수율 69.3%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
0 °C

실험 절차

To a solution of 7-(4-methylbenzyl)benzo[b]thiophene (0.57 g) in tetrahydrofuran (10 mL) was added n-butyllithium (2.71 mol/L tetrahydrofuran solution, 0.88 mL) at −78° C. under an argon atmosphere. The mixture was stirred at the same temperature for 30 minutes and a solution of 2,3,4,6-tetra-O-benzyl-D-glucono-1,5-lactone (1.2 g) in tetrahydrofuran (5 mL) was added to the mixture. The reaction mixture was warmed to 0° C. and stirred for 10 minutes. The reaction mixture was poured into a saturated ammonium chloride aqueous solution, and the mixture was extracted with diethyl ether. The organic layer washed with brine and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=4/1) to give the title compound (1.2 g).

후처리

  1. stirringstirred for 10 minutes
  2. extractionthe mixture was extracted with diethyl ether
  3. washThe organic layer washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was removed under reduced pressure
  6. customthe residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=4/1)

출처 및 근거

ORD 기록
ord-e14b8a23f0c14c4ba48c7fa85ab8d153
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07732596B2

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