3-Hydroxyacetophenone → 3-acetylphenyl 2,3,4-tri-O-acetyl-5-thio-beta-D-xylopyranoside

HRID 6039

反応式

HRID 6039 の反応式
[OH:1][C:2]1[CH:3]=[C:4]([C:8](=[O:10])[CH3:9])[CH:5]=[CH:6][CH:7]=1.[C:11]([O:14][C@@H:15]1[C@@H:20]([O:21][C:22](=[O:24])[CH3:23])[C@H:19]([O:25][C:26](=[O:28])[CH3:27])[CH2:18][S:17][CH:16]1Br)(=[O:13])[CH3:12]>C(Cl)Cl.C(#N)C.[N-]1C=CN=C1.[Ag+].[Cl-].[Zn+2].[Cl-]>[C:11]([O:14][C@@H:15]1[C@@H:20]([O:21][C:22](=[O:24])[CH3:23])[C@H:19]([O:25][C:26](=[O:28])[CH3:27])[CH2:18][S:17][C@H:16]1[O:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8](=[O:10])[CH3:9])[CH:3]=1)(=[O:13])[CH3:12]

参加物

7

反応物 2

HCID 84873-HydroxyacetophenoneHCID 113826832,3,4-Tri-o-acetyl-5-thioxylopyranosyl bromide

生成物 1

HCID 150678523-acetylphenyl 2,3,4-tri-O-acetyl-5-thio-beta-D-xylopyranoside収率 14%

試薬・触媒・溶媒 4

HCID 3007855Zincchloride触媒HCID 10931941Silver imidazolate触媒HCID 6342Acetonitrile溶媒HCID 6344Dichloromethane溶媒

実験手順

If the procedure described in Preparation LXXXIII is followed starting from 3.45 g (25.3.10-3 mol) of 1-(3-hydroxyphenyl)ethanone, 6 g (16.9.10-3 mol) of 2,3,4-tri-O-acetyl-5-thio-D-xylopyranosyl bromide, 3 g (17.10-3 mol) of silver imidazolate and 4.6 g (33.7.10-3 mol) of zinc chloride in 90 ml of methylene chloride and 30 ml of acetonitrile, 0.96 g (yield: 14%) of the expected product is obtained after purification by chromatography on silica gel using a toluene/ethyl acetate mixture (6/1 v/v) as the eluent, and crystallization from ether.

後処理

  1. customIf the procedure described in Preparation LXXXIII

出典と根拠

ORDレコード
ord-fe312a64789d4aa28cb765688102371f
出典データセット
uspto-grants-1993_09
特許番号
US05246961

関連ノート

読み込み中…