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Imidazole → (4R,6S)-4-(tert-butyldimethylsilyloxy)-6-(dimethoxymethyl)-tetrahydropyran-2-one

HRID 1261819
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HRID 1261819 반응식
[CH3:1][O:2][CH:3]([O:12][CH3:13])[C@H:4]1[O:9][C:8](=[O:10])[CH2:7][C@H:6]([OH:11])[CH2:5]1.N1C=CN=C1.[Si:19](Cl)([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20]>ClCCl>[Si:19]([O:11][C@@H:6]1[CH2:5][C@@H:4]([CH:3]([O:12][CH3:13])[O:2][CH3:1])[O:9][C:8](=[O:10])[CH2:7]1)([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20]
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참가 물질

5

반응물 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 67320619(4R,6S)-6-(dimethoxymethyl)-4-hydroxy-tetrahydropyran-2-one

생성물 1

HCID 68898127(4R,6S)-4-(tert-butyldimethylsilyloxy)-6-(dimethoxymethyl)-tetrahydropyran-2-one

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
0 °C

실험 절차

To a solution of 0.5 g of (4R,6S)-6-(dimethoxymethyl)-4-hydroxy-tetrahydropyran-2-one (II′) in 50 mL of dichloromethane, 280 mg of imidazole are added at 25° C. After cooling to 0° C., 400 mg of tert-butyldimethylsilyl chloride are added. The reaction mixture is then stirred for 18 hours and dichloromethane is distilled off. The residue is flash chromatographed (DIPE/acetonitrile=5/1). The solvents are distilled off to get the title compound.

후처리

  1. distillationdichloromethane is distilled off
  2. customchromatographed (DIPE/acetonitrile=5/1)
  3. distillationThe solvents are distilled off

출처 및 근거

ORD 기록
ord-babc51b1eb5f46fa853faba05db0af10
출처 데이터셋
uspto-grants-2013_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08471045B2

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