4'-Mercaptoacetanilide → 4-acetamidophenyl 2,3,4-tri-O-acetyl-1,5dithio-beta-D-xylopyranoside

HRID 6026

Reaktionsgleichung

Reaktionsgleichung von HRID 6026
[SH:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:11])[CH3:10])=[CH:4][CH:3]=1.[C:12]([O:15][C@@H:16]1[C@@H:21]([O:22][C:23](=[O:25])[CH3:24])[C@H:20]([O:26][C:27](=[O:29])[CH3:28])[CH2:19][S:18][CH:17]1Br)(=[O:14])[CH3:13]>[O-2].[Zn+2]>[C:12]([O:15][C@@H:16]1[C@@H:21]([O:22][C:23](=[O:25])[CH3:24])[C@H:20]([O:26][C:27](=[O:29])[CH3:28])[CH2:19][S:18][C@H:17]1[S:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9](=[O:11])[CH3:10])=[CH:6][CH:7]=1)(=[O:14])[CH3:13]

Komponenten

4

Edukt 2

HCID 707774'-MercaptoacetanilideHCID 113826832,3,4-Tri-o-acetyl-5-thioxylopyranosyl bromide

Produkt 1

HCID 538354914-acetamidophenyl 2,3,4-tri-O-acetyl-1,5dithio-beta-D-xylopyranosideAusbeute 25 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3007857Zinc OxideKatalysator

Versuchsvorschrift

If the procedure described in Preparation IV is followed starting from 4.5 g (27.10-3 mol) of N-(4-mercaptophenyl)acetamide, 11.43 g (32.10-3 mol) of 2,3,4-tri-O-acetyl-5-thio-D-xylopyranosyl bromide and 2.16 g (27.10-3 mol) of zinc oxide (ZnO), 3 g (yield: 25%) of the expected product are obtained after recrystallization from a toluene/isopropyl ether mixture.

Quellen und Nachweise

ORD-Eintrag
ord-2f66ead790264f6bbe1372504f543aaf
Quelldatensatz
uspto-grants-1993_09
Patentnummer
US05246961

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