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

HRID 6043

반응식

HRID 6043 반응식
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[C:5]#[N:6].[C:10]([O:13][C@@H:14]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:15]1Br)(=[O:12])[CH3:11]>C(Cl)Cl.[N-]1C=CN=C1.[Ag+].[Cl-].[Zn+2].[Cl-]>[C:10]([O:13][C@@H:14]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:15]1[O:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:4]([C:5]#[N:6])[CH:3]=1)(=[O:12])[CH3:11]

참가 물질

6

반응물 2

HCID 133943-CyanophenolHCID 109263142,3,4-tri-O-acetyl-5-thio-alpha-xylopyranosyl bromide

생성물 1

HCID 150678563-cyanophenyl 2,3,4-tri-O-acetyl-5-thio-beta-D-xylopyranoside수율 33.3%

시약·촉매·용매 3

HCID 3007855Zincchloride촉매HCID 10931941Silver imidazolate촉매HCID 6344Dichloromethane용매

실험 절차

If the procedure described in Preparation LXXXIII is followed starting from 2 g (16.8.10-3 mol) of 3-hydroxybenzonitrile, 2.9 mg (16.5.10-3 mol) of silver imidazolate, 6.5 g (18.3.10-3 mol) of 2,3,4-tri-O-acetyl-5-thio-α-D-xylopyranosyl bromide and 4.6 g (33.6.10-3 mol) of zinc chloride in 80 ml of methylene chloride, 2.2 g (yield: 33%) of the expected product are obtained after purification by chromatography on silica gel using a hexane/ethyl acetate mixture (3/1 v/v) as the eluent, and precipitation in ether.

후처리

  1. customIf the procedure described in Preparation LXXXIII

출처 및 근거

ORD 기록
ord-9094a061a11242d6a707afb2325720a6
출처 데이터셋
uspto-grants-1993_09
특허 번호
US05246961

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