4-羟基苯甲腈 → 4-cyanophenyl 2,3,4-tri-O-acetyl-5-thio-beta-D-xylopyranoside

HRID 6029

反应方程式

HRID 6029 反应方程式
[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]

参与物

6

反应物 2

HCID 130194-羟基苯甲腈HCID 113826832,3,4-Tri-o-acetyl-5-thioxylopyranosyl bromide

产物 1

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

试剂、催化剂与溶剂 3

HCID 3007857氧化锌催化剂HCID 1140甲苯溶剂HCID 6342乙腈溶剂

反应条件

温度
50 °C

实验过程

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.

后处理

  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

来源与证据

ORD记录
ord-e7b03201d99f4d3da974587d2d9e325c
来源数据集
uspto-grants-1993_09
专利号
US05246961

关联笔记

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