Reaktion #6106

ord-e8f938242b2b48989838b82c5425b8d6

Reaktionsgleichung

Sc1ccccc1
benzenethiol
CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@@H](Br)SC[C@H]1OC(C)=O
2,3,4-tri-O-acetyl-5-thio-α-D-xylopyranosyl bromide
→
CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](Sc2ccccc2)SC[C@H]1OC(C)=O
expected product
Ausbeute 32.3%
CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](Sc2ccccc2)SC[C@H]1OC(C)=O
phenyl 2,3,4-tri-O-acetyl-1,5-dithio-β-D-xylopyranoside
Ausbeute 32.3%

Edukte

—
IV
Sc1ccccc1
benzenethiol
CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@@H](Br)SC[C@H]1OC(C)=O
2,3,4-tri-O-acetyl-5-thio-α-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 g (36.3.10-3 mol) of benzenethiol, 15 g (42.3.10-3 mol) of 2,3,4-tri-O-acetyl-5-thio-α-D-xylopyranosyl bromide and 3 g (36.8.10-3 mol) of zinc oxide (ZnO), 4.5 g (yield: 32.29%) of the expected product are obtained after crystallization from ether.

Quelle

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