Thiophenol → 1-Thiophenyl-3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-beta-D-glucopyranose

HRID 129999노트

반응식

HRID 129999 반응식
C([O:4][C@@H:5]1[O:18][C@H:17]([CH2:19][O:20][C:21](=[O:23])[CH3:22])[C@@H:12]([O:13][C:14](=[O:16])[CH3:15])[C@H:7]([O:8][C:9](=[O:11])[CH3:10])[C@H:6]1[N:24]1[C:28](=[O:29])[C:27]2=[CH:30][CH:31]=[CH:32][CH:33]=[C:26]2[C:25]1=[O:34])(=O)C.[C:35]1([SH:41])[CH:40]=[CH:39][CH:38]=CC=1.[Sn](Cl)(Cl)(Cl)Cl>ClCCl>[S:41]1[CH:35]=[CH:40][CH:39]=[C:38]1[C@:5]1([O:18][C@H:17]([CH2:12][O:13][C:14](=[O:16])[CH3:15])[C@@H:19]([O:20][C:21](=[O:23])[CH3:22])[C@H:7]([O:8][C:9](=[O:11])[CH3:10])[C@H:6]1[N:24]1[C:25](=[O:34])[C:26]2=[CH:33][CH:32]=[CH:31][CH:30]=[C:27]2[C:28]1=[O:29])[OH:4]

참가 물질

5

반응물 3

HCID 7969ThiophenolHCID 24287Tin tetrachlorideHCID 2728904beta-D-Glucopyranose, 2-deoxy-2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-, 1,3,4,6-tetraacetate

생성물 1

HCID 867491291-Thiophenyl-3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-beta-D-glucopyranose

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

The product compound [2] (0.31-8.02 g, 0.68-17.7 mmol) is dissolved in 3.2-100 ml of dry dichloromethane, and thiophenol (0.15-3.9 g, 1.36-35.4 mmol) and tin tetrachloride (0.35-9.22 g, 1.36-35.4 mmol) are added and the mixture is stirred until reaction is complete. The reaction mixture is diluted and then washed with saturated sodium bicarbonate solution. Concentration results in the crude product compound [3]. Purification takes place by chromatography on silica gel with an ethyl acetate/isohexane gradient (0.27-71.4 g, 0.54-14.2 mmol, about 80%). FAB-MS: M+H+ =504. NMR data consistent with Nicolaou et al., J. Am. Chem. Soc. 112:3695 (1990) and T. J. Caulfield, Ph.D. Dissertation, the University of Pennsylvania (1991).

후처리

  1. additionThe reaction mixture is diluted
  2. washwashed with saturated sodium bicarbonate solution
  3. concentrationConcentration

출처 및 근거

ORD 기록
ord-71215258f16e4b85b337786d87955c96
출처 데이터셋
uspto-grants-1995_11
특허 번호
US05470843

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