2,3,4-tri-O-acetyl-5-thio-alpha-xylopyranosyl bromide → 3-cyanophenyl 2,3,4-tri-O-acetyl-1,5-dithio-beta-D-xylopyranoside

HRID 6003

Reaktionsgleichung

Reaktionsgleichung von HRID 6003
[SH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[C:5]#[N:6].[C:10]([O:13][C@@H:14]1[C@@H:19]([O:20][C:21](=[O:23])[CH3:22])[C@H:18]([O:24][C:25](=[O:27])[CH3:26])[CH2:17][S:16][C@@H:15]1Br)(=[O:12])[CH3:11]>[O-2].[Zn+2]>[C:10]([O:13][C@@H:14]1[C@@H:19]([O:20][C:21](=[O:23])[CH3:22])[C@H:18]([O:24][C:25](=[O:27])[CH3:26])[CH2:17][S:16][C@H:15]1[S:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:4]([C:5]#[N:6])[CH:3]=1)(=[O:12])[CH3:11]

Komponenten

4

Edukt 2

HCID 109263142,3,4-tri-O-acetyl-5-thio-alpha-xylopyranosyl bromideHCID 147953343-Sulfanylbenzonitrile

Produkt 1

HCID 147953433-cyanophenyl 2,3,4-tri-O-acetyl-1,5-dithio-beta-D-xylopyranosideAusbeute 31 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3007857Zinc OxideKatalysator

Versuchsvorschrift

If the procedure described in Preparation IV is followed starting from 10.3 g (74.1.10-3 mol) of 3-mercaptobenzonitrile, 28.94 g (81.5.10-3 mol) of 2,3,4-tri-O-acetyl-5-thio-α-D-xylopyranosyl bromide and 6.05 g (74.3.10-3 mol) of zinc oxide (ZnO), 9.6 g (yield: 31%) of the expected product are obtained.

Quellen und Nachweise

ORD-Eintrag
ord-3797a11312aa4e1d97071f5559443167
Quelldatensatz
uspto-grants-1993_09
Patentnummer
US05246961

Verknüpfte Notizen

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