Ethanol → 4-cyanophenyl 2,3,4-tri-O-acetyl-5-thio-beta-D-xylopyranoside

HRID 6027

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HRID 6027 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].[OH:20][C:21]1[CH:28]=[CH:27][C:24]([C:25]#[N:26])=[CH:23][CH:22]=1.C(O)C>C(Cl)Cl.[Cl-].[Zn+2].[Cl-].[N-]1C=CN=C1.[Ag+]>[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:20][C:21]1[CH:28]=[CH:27][C:24]([C:25]#[N:26])=[CH:23][CH:22]=1)(=[O:3])[CH3:2]

참가 물질

7

반응물 3

HCID 702EthanolHCID 130194-CyanophenolHCID 109263142,3,4-tri-O-acetyl-5-thio-alpha-xylopyranosyl bromide3회

생성물 1

HCID 150678464-cyanophenyl 2,3,4-tri-O-acetyl-5-thio-beta-D-xylopyranoside수율 112.5%

시약·촉매·용매 3

HCID 3007855Zincchloride촉매2회HCID 10931941Silver imidazolate촉매2회HCID 6344Dichloromethane용매

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온도
40 °C

실험 절차

A suspension of 6.5 g (12.3.10-3 mol) of 2,3,4-tri-O-acetyl-5-thio-α-D-xylopyranosyl bromide, 6 g (50.4.10-3 mol) of 4-hydroxybenzonitrile, 6.9 g (50.5.10-3 mol) of zinc chloride and 4.4 g (25.1.10-3 mol) of silver imidazolate in 200 ml of anhydrous methylene chloride is stirred at 40° C., under an inert atmosphere, in the absence of light and in the presence of a molecular sieve (400 pm). After 7 h at this temperature, 6.9 g (50.5.10-3 mol) of zinc chloride, 4.4 g (25.1.10-3 mol) of silver imidazolate and 6.5 g (18.3.10-3 mol) of 2,3,4-tri-O-acetyl-5-thio-α-D-xylopyranosyl bromide are added. The reaction medium is left overnight under these conditions and 6.5 g (12.3.10-3 mol) of 2,3,4-tri-O-acetyl-5-thio-α-D-xylopyranosyl bromide are then added. After 24 h, the reaction mixture is filtered on Celite® , washed with a 1N aqueous solution of hydrochloric acid and then water and dried over magnesium sulfate. After evaporation under reduced pressure, the residue is purified by chromatography on silica gel using a hexane/ethyl acetate mixture (3/1 v/v) as the eluent. 8.1 g (yield:41%) of the expected product are obtained by crystallization from ethanol.

후처리

  1. additionare then added
  2. filtrationthe reaction mixture is filtered on Celite®
  3. washwashed with a 1N aqueous solution of hydrochloric acid
  4. dry with materialwater and dried over magnesium sulfate
  5. customAfter evaporation under reduced pressure
  6. customthe residue is purified by chromatography on silica gel using a hexane/ethyl acetate mixture (3/1 v/v) as the eluent

출처 및 근거

ORD 기록
ord-4b2ec04873ae4d519d8ca8b0c0b1965c
출처 데이터셋
uspto-grants-1993_09
특허 번호
US05246961

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