Reaktion #6122

ord-2f66ead790264f6bbe1372504f543aaf

Reaktionsgleichung

CC(=O)Nc1ccc(S)cc1
N-(4-mercaptophenyl)acetamide
CC(=O)O[C@H]1[C@H](OC(C)=O)CSC(Br)[C@@H]1OC(C)=O
2,3,4-tri-O-acetyl-5-thio-D-xylopyranosyl bromide
→
CC(=O)Nc1ccc(S[C@@H]2SC[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]2OC(C)=O)cc1
expected product
Ausbeute 25.0%
CC(=O)Nc1ccc(S[C@@H]2SC[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]2OC(C)=O)cc1
4-acetamidophenyl 2,3,4-tri-O-acetyl-1,5-dithio-β-D-xylopyranoside
Ausbeute 25.0%

Edukte

—
IV
CC(=O)Nc1ccc(S)cc1
N-(4-mercaptophenyl)acetamide
CC(=O)O[C@H]1[C@H](OC(C)=O)CSC(Br)[C@@H]1OC(C)=O
2,3,4-tri-O-acetyl-5-thio-D-xylopyranosyl bromide

Reagenzien

[O-2].[Zn+2]
zinc oxide

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Vorschrift

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.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05246961uspto-grants-1993_09