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

HRID 2373007

反応式

HRID 2373007 の反応式
[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]

参加物

6

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 3007855Zincchloride触媒HCID 10931941Silver imidazolate触媒HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  1. customIf the procedure described in Preparation LXXXIII

出典と根拠

ORDレコード
ord-f8f4ef1095dd4e8c90dc9275c59b2f94
出典データセット
uspto-grants-1992_03
特許番号
US05101048

関連ノート

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