Benzyl Bromide → [[(2R,3R,4S,5R,6S)-3,4,5-tribenzyloxy-6-[4-chloro-3-[[4-(trifluoromethoxy)phenyl]methyl]phenyl]-6-methoxy-tetrahydropyran-2-yl]methoxy]tert-butyl-dimethyl-silane

HRID 1055535노트

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HRID 1055535 반응식
[Si:1]([O:8][CH2:9][C@H:10]1[O:15][C@:14]([C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[C:20]([CH2:25][C:26]3[CH:31]=[CH:30][C:29]([O:32][C:33]([F:36])([F:35])[F:34])=[CH:28][CH:27]=3)[CH:19]=2)([O:16][CH3:17])[C@H:13]([OH:37])[C@@H:12]([OH:38])[C@@H:11]1[OH:39])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[H-].[Na+].[CH2:42](Br)[C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1>O1CCCC1.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[C:4]([Si:1]([CH3:3])([CH3:2])[O:8][CH2:9][C@@H:10]1[C@@H:11]([O:39][CH2:42][C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[C@H:12]([O:38][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C@@H:13]([O:37][CH2:14][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C@@:14]([C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[C:20]([CH2:25][C:26]3[CH:31]=[CH:30][C:29]([O:32][C:33]([F:36])([F:35])[F:34])=[CH:28][CH:27]=3)[CH:19]=2)([O:16][CH3:17])[O:15]1)([CH3:6])([CH3:7])[CH3:5]

참가 물질

6

반응물 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 86685138(2S,3R,4S,5S,6R)-6-[(tert-butyl(dimethyl)silyl)oxymethyl]-2-[4-chloro-3-[[4-(trifluoromethoxy)phenyl]methyl]phenyl]-2-methoxy-tetrahydropyran-3,4,5-triol

생성물 1

HCID 86685139[[(2R,3R,4S,5R,6S)-3,4,5-tribenzyloxy-6-[4-chloro-3-[[4-(trifluoromethoxy)phenyl]methyl]phenyl]-6-methoxy-tetrahydropyran-2-yl]methoxy]tert-butyl-dimethyl-silane수율 260.4%

시약·촉매·용매 2

HCID 67553Tetrabutylammonium Iodide촉매HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

To a solution of (2S,3R,4S,5S,6R)-6-[[tert-butyl(dimethyl)silyl]oxymethyl]-2-[4-chloro-3-[[4-(trifluoromethoxy)phenyl]methyl]phenyl]-2-methoxy-tetrahydropyran-3,4,5-triol 15i (1.37 g, 1.69 mmol) in anhydrous tetrahydrofuran (15 mL) was added sodium hydride (0.20 g, 8.45 mmol, 60% dispersion in Mineral oil) at 0° C. The mixture was stirred at 0° C. for 15 min, and then benzyl bromide (1.45 g, 8.45 mmol) and tetrabutylammonium iodide (0.06 g, 0.17 mmol) were added in turn. The mixture was further stirred at room temperature for 20 hours. The reaction mixture was quenched with water (10 mL) and extracted with ethyl acetate (20 mL). The aqueous layer was extracted with ethyl acetate (20 mL×3). The combined organic layers were washed with saturated brine (20 mL×3), dried over anhydrous sodium sulfate, filtered. The filtrate was concentrated in vacuo to give the title compound 15j as yellow oil (1.9 g, 100%). This material was not further purified.

후처리

  1. stirringThe mixture was further stirred at room temperature for 20 hours
  2. customThe reaction mixture was quenched with water (10 mL)
  3. extractionextracted with ethyl acetate (20 mL)
  4. extractionThe aqueous layer was extracted with ethyl acetate (20 mL×3)
  5. washThe combined organic layers were washed with saturated brine (20 mL×3)
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated in vacuo

출처 및 근거

ORD 기록
ord-9e6e50e0595348ca8e28b645b1dc9cbc
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09394329B2

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