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

HRID 5994

반응식

HRID 5994 반응식
[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]

참가 물질

6

반응물 2

HCID 5850584-ThiobenzonitrileHCID 109263142,3,4-tri-O-acetyl-5-thio-alpha-xylopyranosyl bromide

생성물 1

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

시약·촉매·용매 3

HCID 3007857Zinc Oxide촉매HCID 1140Toluene용매HCID 6342Acetonitrile용매

반응 조건

온도
50 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-c325c2e4bd414d69a18ffb5e8f24076c
출처 데이터셋
uspto-grants-1993_09
특허 번호
US05246961

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