反応 #6120

ord-20ce36ae2e6848d387fd32a102b78617

反応方程式

N#Cc1cc(C#N)c(S)c(C#N)c1
3,5-dicyano-2-mercaptobenzonitrile
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
N#[C][Hg][C]#N
mercuric cyanide
N#[C][Hg][C]#N
Hg(CN)2
→
CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](Sc2c(C#N)cc(C#N)cc2C#N)SC[C@H]1OC(C)=O
expected product
収率 17.0%
CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](Sc2c(C#N)cc(C#N)cc2C#N)SC[C@H]1OC(C)=O
2,4,6-tricyanophenyl 2,3,4-tri-O-acetyl-1,5-dithio-β-D-xylopyranoside
収率 17.0%

反応物

N#Cc1cc(C#N)c(S)c(C#N)c1
3,5-dicyano-2-mercaptobenzonitrile
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
N#[C][Hg][C]#N
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 4.8 g (258.10-3 mol) of 3,5-dicyano-2-mercaptobenzonitrile (Example 17a), 9.71 g (258.10-3 mol) of 2,3,4-tri-O-acetyl-5-thio-α-D-xylopyranosyl bromide and 6.57 g (8.6.10-3 mol) of mercuric cyanide (Hg(CN)2), 2 g (yield: 17%) of the expected product are obtained after crystallization from ether.

出典

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