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

HRID 2372993

反応式

HRID 2372993 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][CH:6]1Br)(=[O:3])[CH3:2].[OH:20][C:21]1[CH:28]=[CH:27][C:24]([C:25]#[N:26])=[CH:23][CH:22]=1>C1(C)C=CC=CC=1.C(#N)C.[O-2].[Zn+2]>[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:20][C:21]1[CH:28]=[CH:27][C:24]([C:25]#[N:26])=[CH:23][CH:22]=1)(=[O:3])[CH3:2]

参加物

6

反応物 2

HCID 130194-CyanophenolHCID 113826832,3,4-Tri-o-acetyl-5-thioxylopyranosyl bromide

生成物 1

HCID 150678464-cyanophenyl 2,3,4-tri-O-acetyl-5-thio-beta-D-xylopyranoside収率 35%

試薬・触媒・溶媒 3

HCID 3007857Zinc Oxide触媒HCID 1140Toluene溶媒HCID 6342Acetonitrile溶媒

反応条件

温度
50 °C

実験手順

A suspension of 0.5 g (1.4.10-3 mol) of 2,3,4-tri-O-acetyl-5-thio-D-xylopyranosyl bromide, 0.25 g (2.1.10-3 mol) of 4-hydroxybenzonitrile and 170 mg (2.1.10-3 mol) of zinc oxide (ZnO) in 4 ml of anhydrous toluene and 4 ml of acetonitrile is stirred at 50° C., under an inert atmosphere, in the presence of a molecular sieve (1 nm), for 48 h. The reaction medium is subsequently filtered on Celite® in ethyl acetate and then washed with a 1N aqueous solution of hydrochloric acid, water, a 1N solution of sodium hydroxide and then a saturated solution of NaCl. The solution obtained is dried over sodium sulfate and the solvent is evaporated off under reduced pressure. The residue obtained is purified by chromatography on silica gel using a hexane/ethyl acetate mixture (2/1 v/v) as the eluent to give 194 mg (yield: 35%) of the expected product.

後処理

  1. filtrationThe reaction medium is subsequently filtered on Celite® in ethyl acetate
  2. washwashed with a 1N aqueous solution of hydrochloric acid, water
  3. customThe solution obtained
  4. dry with materialis dried over sodium sulfate
  5. customthe solvent is evaporated off under reduced pressure
  6. customThe residue obtained
  7. customis purified by chromatography on silica gel using a hexane/ethyl acetate mixture (2/1 v/v) as the eluent

出典と根拠

ORDレコード
ord-fcdf50ea001d41dbac6abbab76a4e9e1
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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