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

HRID 6036

反応式

HRID 6036 の反応式
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=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][C@@H:16]1Br)(=[O:13])[CH3:12]>C(Cl)Cl.[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][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=1)(=[O:13])[CH3:12]

参加物

6

反応物 2

HCID 74694'-HydroxyacetophenoneHCID 109263142,3,4-tri-O-acetyl-5-thio-alpha-xylopyranosyl bromide

生成物 1

HCID 150678504-acetylphenyl 2,3,4-tri-O-acetyl-5-thio-beta-D-xylopyranoside収率 18%

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 (14.7.10-3 mol) of 1-(4-hydroxyphenyl)ethanone, 2.8 g (16.10-3 mol) of silver imidazolate, 5.74 g (16.1.10-3 mol) of 2,3,4-tri-O-acetyl-5-thio-α-D-xylopyranosyl bromide and 4 g (29.3.10-3 mol) of zinc chloride in 100 ml of methylene chloride, 0.96 g (yield: 18%) 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.

後処理

  1. customIf the procedure described in Preparation LXXXIII

出典と根拠

ORDレコード
ord-2e92d2415ae14a2c94e457a5f31e7891
出典データセット
uspto-grants-1993_09
特許番号
US05246961

関連ノート

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