o-Nitrobenzenethiol → 2-nitrophenyl 2,3,4-tri-O-acetyl-1,5-dithio-beta-D-xylopyranoside

HRID 6008

Reaktionsgleichung

Reaktionsgleichung von HRID 6008
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[SH:10])([O-:3])=[O:2].[C:11]([O:14][C@@H:15]1[C@@H:20]([O:21][C:22](=[O:24])[CH3:23])[C@H:19]([O:25][C:26](=[O:28])[CH3:27])[CH2:18][S:17][C@@H:16]1Br)(=[O:13])[CH3:12]>[O-2].[Zn+2]>[C:11]([O:14][C@@H:15]1[C@@H:20]([O:21][C:22](=[O:24])[CH3:23])[C@H:19]([O:25][C:26](=[O:28])[CH3:27])[CH2:18][S:17][C@H:16]1[S:10][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[N+:1]([O-:3])=[O:2])(=[O:13])[CH3:12]

Komponenten

4

Edukt 2

HCID 21002o-NitrobenzenethiolHCID 109263142,3,4-tri-O-acetyl-5-thio-alpha-xylopyranosyl bromide

Produkt 1

HCID 147953472-nitrophenyl 2,3,4-tri-O-acetyl-1,5-dithio-beta-D-xylopyranosideAusbeute 58,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3007857Zinc OxideKatalysator

Versuchsvorschrift

If the procedure described in Preparation IV is followed starting from 6.1 g (39.3.10-3 mol) of 2-nitrobenzenethiol, 15.40 g (43.3.10-3 mol) of 2,3,4-tri-O-acetyl-5-thio-α-D-xylopyranosyl bromide and 3.68 g (45.2.10-3 mol) of zinc oxide (ZnO), 9.87 g (yield: 58%) of the expected product are obtained.

Quellen und Nachweise

ORD-Eintrag
ord-3e2d878ec29b4bfc9297a97ac3acc1b2
Quelldatensatz
uspto-grants-1993_09
Patentnummer
US05246961

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