Trichloroacetonitrile → 2,3,4-tri-O-acetyl-5-thio-alpha-D-xylopyranosyl trichloroacetimidate

HRID 6031

반응식

HRID 6031 반응식
[Cl:1][C:2]([Cl:6])([Cl:5])[C:3]#[N:4].[H-].[Na+].[C:9]([O:12][C@@H:13]1[C@@H:19]([O:20][C:21](=[O:23])[CH3:22])[C@H:18]([O:24][C:25](=[O:27])[CH3:26])[CH2:17][S:16][C@@H:14]1[OH:15])(=[O:11])[CH3:10]>C(Cl)Cl>[Cl:1][C:2]([Cl:6])([Cl:5])[C:3](=[NH:4])[O:15][C@H:14]1[S:16][CH2:17][C@@H:18]([O:24][C:25](=[O:27])[CH3:26])[C@H:19]([O:20][C:21](=[O:23])[CH3:22])[C@H:13]1[O:12][C:9](=[O:11])[CH3:10]

참가 물질

5

반응물 3

HCID 11011TrichloroacetonitrileHCID 24758Sodium hydrideHCID 232401882,3,4-tri-O-acetyl-5-thio-alpha-D-xylopyranose

생성물 1

HCID 216315472,3,4-tri-O-acetyl-5-thio-alpha-D-xylopyranosyl trichloroacetimidate수율 53%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

1.5 ml (15.10-3 mol) of trichloroacetonitrile and 70 mg of NaH (2.3.10-3 mol of NaH in 80% dispersion) are added to a solution of 1 g (3.42.10-3 mol) of 2, 3, 4 -tri-O-acetyl-5-thio-α-D-xylopyranose in 10 ml of methylene chloride. After 4 h at room temperature, the reaction medium is filtered on silica in methylene chloride and then purified by chromatography on silica gel using a hexane/ethyl acetate mixture (3/1 v/v) as the eluent. 790 mg (yield: 53%) of the expected product are obtained after crystallization from an ethyl acetate/hexane mixture.

후처리

  1. filtrationthe reaction medium is filtered on silica in methylene chloride
  2. custompurified by chromatography on silica gel using a hexane/ethyl acetate mixture (3/1 v/v) as the eluent

출처 및 근거

ORD 기록
ord-aa359b71c3c249e1a1f6ac726e50d826
출처 데이터셋
uspto-grants-1993_09
특허 번호
US05246961

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