2-Nitrophenol → 2-nitrophenyl 2,3,4-tri-O-acetyl-5-thio-beta-D-xylopyranoside

HRID 6046

反応式

HRID 6046 の反応式
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[OH:10])([O-:3])=[O:2].[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:10][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[N+:1]([O-:3])=[O:2])(=[O:13])[CH3:12]

参加物

6

反応物 2

HCID 69472-NitrophenolHCID 109263142,3,4-tri-O-acetyl-5-thio-alpha-xylopyranosyl bromide

生成物 1

HCID 150678582-nitrophenyl 2,3,4-tri-O-acetyl-5-thio-beta-D-xylopyranoside収率 15.3%

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 (14.4.10-3 mol) of 2-nitrophenol, 2.5 g (14.2.10-3 mol) of silver imidazolate, 6 g (15.7.10-3 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 80 ml of methylene chloride, 0.91 g (yield: 15%) of the expected product is obtained after purification by chromatography on silica gel using a hexane/ethyl acetate mixture (2/1 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-06ef2526ca4b4e82962cc682dc5f8a8a
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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