4-Thiobenzonitrile → 4-cyanophenyl 2,3,4-tri-O-acetyl-1,5-dithio-beta-D-xylopyranoside

HRID 5994

反応式

HRID 5994 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].[SH: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[S: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 5850584-ThiobenzonitrileHCID 109263142,3,4-tri-O-acetyl-5-thio-alpha-xylopyranosyl bromide

生成物 1

HCID 147953324-cyanophenyl 2,3,4-tri-O-acetyl-1,5-dithio-beta-D-xylopyranoside収率 64%

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 16.9 g (47.10-3 mol) of 2,3,4-tri-O-acetyl-5-thio-α-D-xylopyranosyl bromide, 6 g (43.10-3 mol) of 4-mercaptobenzonitrile and 3.5 g (43.10-3 mol) of zinc oxide (ZnO) in 120 ml of anhydrous toluene and 120 ml of acetonitrile is stirred under an inert atmosphere, in the presence of a molecular sieve (1 mm), for 18 hours, at 50° C. After the reaction medium has been filtered on Celite® in ethyl acetate, the organic phase obtained is washed with a 1N solution of HCl twice, a 1N solution of sodium hydroxide and finally water, dried over magnesium sulfate and evaporated under reduced pressure. After precipitation in ether, 11.30 g (yield: 64%) of the expected product are obtained.

後処理

  1. filtrationAfter the reaction medium has been filtered on Celite® in ethyl acetate
  2. customthe organic phase obtained
  3. washis washed with a 1N solution of HCl twice
  4. dry with materiala 1N solution of sodium hydroxide and finally water, dried over magnesium sulfate
  5. customevaporated under reduced pressure
  6. customAfter precipitation in ether

出典と根拠

ORDレコード
ord-c325c2e4bd414d69a18ffb5e8f24076c
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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