반응 #2460153

ord-81a3a601463540d9b7c9d84811812908

반응 방정식

O=[N+]([O-])c1ccccc1S
2-nitrobenzenethiol
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[N+](=O)[O-])SC[C@H]1OC(C)=O
expected product
수율 58.5%
CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](Sc2ccccc2[N+](=O)[O-])SC[C@H]1OC(C)=O
2-nitrophenyl 2,3,4-tri-O-acetyl-1,5-dithio-β-D-xylopyranoside
수율 58.5%

반응물

—
IV
O=[N+]([O-])c1ccccc1S
2-nitrobenzenethiol
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

시약

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

반응 조건

상세 조건
See reaction.notes.procedure_details.

실험 절차

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.

출처

DOI: 10.6084/m9.figshare.5104873.v1특허: US05101048uspto-grants-1992_03