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

HRID 5993

Reaktionsgleichung

Reaktionsgleichung von HRID 5993
ClC(Cl)(Cl)C(=N)O[C@H:5]1[S:22][CH2:21][C@@H:16]([O:17][C:18](=[O:20])[CH3:19])[C@H:11]([O:12][C:13](=[O:15])[CH3:14])[C@H:6]1[O:7][C:8](=[O:10])[CH3:9].[SH:26][C:27]1[CH:34]=[CH:33][C:30]([C:31]#[N:32])=[CH:29][CH:28]=1>C(#N)C.[Cl-].[Zn+2].[Cl-]>[C:8]([O:7][C@@H:6]1[C@@H:11]([O:12][C:13](=[O:15])[CH3:14])[C@H:16]([O:17][C:18](=[O:20])[CH3:19])[CH2:21][S:22][C@H:5]1[S:26][C:27]1[CH:34]=[CH:33][C:30]([C:31]#[N:32])=[CH:29][CH:28]=1)(=[O:10])[CH3:9]

Komponenten

5

Edukt 2

HCID 5850584-ThiobenzonitrileHCID 216315472,3,4-tri-O-acetyl-5-thio-alpha-D-xylopyranosyl trichloroacetimidate

Produkt 1

HCID 147953324-cyanophenyl 2,3,4-tri-O-acetyl-1,5-dithio-beta-D-xylopyranosideAusbeute 23 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3007855ZincchlorideKatalysatorHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A suspension of 192 mg (0.44.10-3 mol) of 2,3,4-tri-O-acetyl-5-thio-α-D-xylopyranosyl trichloroacetimidate, 71 mg (0.52.10-3 mol) of 4-mercaptobenzonitrile, 20 mg (0.15.10-3 mol) of zinc chloride and a 400 pm sieve in 2 ml of acetonitrile is stirred for 4 h under an inert atmosphere. The reaction mixture is then filtered on Celite® in ethyl acetate and subsequently washed with a 1N solution of sodium hydroxide, water and finally a saturated solution of sodium chloride, dried over magnesium sulfate and evaporated under reduced pressure. After precipitation in ether, 42 mg (yield: 23%) of the expected product are obtained.

Aufarbeitung

  1. filtrationThe reaction mixture is then filtered on Celite® in ethyl acetate
  2. washsubsequently washed with a 1N solution of sodium hydroxide, water
  3. dry with materialfinally a saturated solution of sodium chloride, dried over magnesium sulfate
  4. customevaporated under reduced pressure
  5. customAfter precipitation in ether

Quellen und Nachweise

ORD-Eintrag
ord-783281c6407248d1a55de54558cee7a5
Quelldatensatz
uspto-grants-1993_09
Patentnummer
US05246961

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