反応 #6092

ord-6e155a0fcdfe4261a9d6e2ec6bcd8028

反応方程式

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
O=[N+]([O-])c1ccc(S)cc1
4-nitrobenzenethiol
N#[C][Hg][C]#N
Hg(CN)2
→
CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](Sc2ccc([N+](=O)[O-])cc2)SC[C@H]1OC(C)=O
expected product
収率 66.0%
CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](Sc2ccc([N+](=O)[O-])cc2)SC[C@H]1OC(C)=O
4-nitrophenyl 2,3,4-tri-O-acetyl-1,5-dithio-β-D-xylopyranoside
収率 66.0%

反応物

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
O=[N+]([O-])c1ccc(S)cc1
4-nitrobenzenethiol
—
mercuric cyanide
N#[C][Hg][C]#N
Hg(CN)2

試薬

なし

反応条件

詳細条件
See reaction.notes.procedure_details.

後処理

  1. 1
    その他If the procedure described in Preparation I

実験手順

If the procedure described in Preparation I is followed starting from 6 g (38.10-3 mol) of 4-nitrobenzenethiol, 10.7 g (42.10-3 mol) of mercuric cyanide, Hg(CN)2, and 15.1 g (42.10-3 mol) of 2,3,4-tri-O-acetyl-5-thio-α-D-xylopyranosyl bromide, 10.8 g (yield: 66%) of the expected product are obtained.

出典

DOI: 10.6084/m9.figshare.5104873.v1特許: US05246961uspto-grants-1993_09