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

HRID 6034

反応式

HRID 6034 の反応式
[C:1]([O:4][C@@H:5]1[C@@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@H:9]([O:15][C:16](=[O:18])[CH3:17])[CH2:8][S:7][C@@H:6]1Br)(=[O:3])[CH3:2].[N+:20]([C:23]1[CH:28]=[CH:27][C:26]([OH:29])=[CH:25][CH:24]=1)([O-:22])=[O:21]>C(Cl)Cl.CCOCC.[Cl-].[Zn+2].[Cl-].[N-]1C=CN=C1.[Ag+]>[C:1]([O:4][C@@H:5]1[C@@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@H:9]([O:15][C:16](=[O:18])[CH3:17])[CH2:8][S:7][C@H:6]1[O:29][C:26]1[CH:27]=[CH:28][C:23]([N+:20]([O-:22])=[O:21])=[CH:24][CH:25]=1)(=[O:3])[CH3:2]

参加物

7

反応物 2

HCID 9804-NitrophenolHCID 109263142,3,4-tri-O-acetyl-5-thio-alpha-xylopyranosyl bromide

生成物 1

HCID 150678484-nitrophenyl 2,3,4-tri-O-acetyl-5-thio-beta-D-xylopyranoside収率 25.2%

試薬・触媒・溶媒 4

HCID 3007855Zincchloride触媒HCID 10931941Silver imidazolate触媒HCID 3283Diethyl Ether溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
50 °C

実験手順

A suspension of 5.6 g (15.8.10-3 mol) of 2,3,4-tri-O-acetyl-5-thio-α-D-xylopyranosyl bromide, 2 g (14.3.10-3 mol) of 4-nitrophenol, 4 g (29.3.10-3 mol) of zinc chloride and 3.8 g (21.7.10-3 mol) of silver imidazolate in 80 ml of anhydrous methylene chloride is stirred at 50° C., under an inert atmosphere, in the absence of light and in the presence of a molecular sieve (400 pm). After 48 h at this temperature, the reaction mixture is filtered on Celite®, washed with a 1N aqueous solution of hydrochloric acid, then a 1N solution of sodium hydroxide and finally water and dried over magnesium sulfate (MgSO4). After evaporation to dryness, the residue is purified by chromatography on silica gel using a hexane/ethyl acetate mixture (3/1 v/v) as the eluent. 1.5 g (yield: 25%) of the expected product are obtained by precipitation in ether.

後処理

  1. filtrationthe reaction mixture is filtered on Celite®
  2. washwashed with a 1N aqueous solution of hydrochloric acid
  3. dry with materiala 1N solution of sodium hydroxide and finally water and dried over magnesium sulfate (MgSO4)
  4. customAfter evaporation to dryness
  5. customthe residue is purified by chromatography on silica gel using a hexane/ethyl acetate mixture (3/1 v/v) as the eluent

出典と根拠

ORDレコード
ord-b9a267834ffc4d2eb782eaa76b1e6127
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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