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Toluene → 4-Chloro-2-(5-isoxazolyl)-5-methylphenyl 2,3,4-tri-O-acetyl-5-thio-beta-D-xylopyranoside

HRID 907069
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HRID 907069 반응식
[C:1]([O:4][C@@H:5]1[C@@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@H:9]([O:15][C:16](=[O:18])[CH3:17])[CH2:8][S:7][C@@H:6]1Br)(=[O:3])[CH3:2].[Cl:20][C:21]1[C:26]([CH3:27])=[CH:25][C:24]([OH:28])=[C:23]([C:29]2[O:33][N:32]=[CH:31][CH:30]=2)[CH:22]=1.C1(C)C=CC=CC=1>[Cl-].[Zn+2].[Cl-].[N-]1C=CN=C1.[Ag+].C(#N)C>[C:1]([O:4][C@@H:5]1[C@@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@H:9]([O:15][C:16](=[O:18])[CH3:17])[CH2:8][S:7][C@H:6]1[O:28][C:24]1[CH:25]=[C:26]([CH3:27])[C:21]([Cl:20])=[CH:22][C:23]=1[C:29]1[O:33][N:32]=[CH:31][CH:30]=1)(=[O:3])[CH3:2]
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참가 물질

7

반응물 3

HCID 1140TolueneHCID 8540424-Chloro-2-(5-isoxazolyl)-5-methylphenolHCID 109263142,3,4-tri-O-acetyl-5-thio-alpha-xylopyranosyl bromide

생성물 1

HCID 248312314-Chloro-2-(5-isoxazolyl)-5-methylphenyl 2,3,4-tri-O-acetyl-5-thio-beta-D-xylopyranoside수율 10%

시약·촉매·용매 3

HCID 3007855Zincchloride
촉매
HCID 10931941Silver imidazolate촉매
HCID 6342Acetonitrile용매

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온도
80 °C

실험 절차

A mixture of 0.8 g (5.87 mmol) of zinc chloride, 2 g of 13× molecular sieve, 2 g (5.6 mmol) of 2,3,4-tri-O-acetyl-5-thio-α-D-xylopyranosyl bromide, 1 g (4.77 mmol) of 4-chloro-2-(5-isoxazolyl)-5-methylphenol, 1 g (5.7 mmol) of silver imidazolate, 5 ml of toluene and 5 ml of acetonitrile is prepared. The mixture is kept stirred at 80° C. for 90 minutes and then cooled and filtered. The residual solid is rinsed on the filter with methanol and the combined filtrates are concentrated under reduced pressure. The crude product obtained is purified by chromatography on silica gel, elution being carried out using a dichloromethane/ethyl acetate mixture (9/1; v/v). The pure fraction is crystallized from ethyl ether. The expected compound is thus obtained in the form of a white solid with a yield of 10%.

후처리

  1. customis prepared
  2. temperaturecooled
  3. filtrationfiltered
  4. washThe residual solid is rinsed on the
  5. filtrationfilter with methanol
  6. concentrationthe combined filtrates are concentrated under reduced pressure
  7. customThe crude product obtained
  8. customis purified by chromatography on silica gel, elution
  9. customThe pure fraction is crystallized from ethyl ether

출처 및 근거

ORD 기록
ord-11ee1b2f8c374600a95f8a22fe0cc99f
출처 데이터셋
uspto-grants-2011_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08013010B2

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