반응 #6108

ord-86b0005ef8c14e33b6bf5c9a49e82eb2

반응 방정식

O=[N+]([O-])c1cccc(S)c1
3-nitrobenzenethiol
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](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](Sc2cccc([N+](=O)[O-])c2)SC[C@H]1OC(C)=O
expected product
수율 27.0%
CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](Sc2cccc([N+](=O)[O-])c2)SC[C@H]1OC(C)=O
3-nitrophenyl 2,3,4-tri-O-acetyl-1,5-dithio-β-D-xylopyranoside
수율 27.0%

반응물

O=[N+]([O-])c1cccc(S)c1
3-nitrobenzenethiol
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](Br)SC[C@H]1OC(C)=O
2,3,4-tri-O-acetyl-5-thio-α-D-xylopyranosyl bromide

시약

없음

반응 조건

상세 조건
See reaction.notes.procedure_details.

후처리

  1. 1
    기타If the procedure described in Preparation I

실험 절차

If the procedure described in Preparation I is followed starting from 10 g (64.5.10-3 mol) of 3-nitrobenzenethiol, 16.29 g (64.5.10-3 mol) of mercuric cyanide (Hg(CN)2) and 25.2 g (70.9.10-3 mol) of 2,3,4-tri-O-acetyl-5-thio-α-D-xylopyranosyl bromide, 7.44 g (yield: 27%) of the expected product are obtained after purification by flash chromatography using a toluene/ethyl acetate mixture (9/1 v/v) as the eluent, followed by crystallization from ether.

출처

DOI: 10.6084/m9.figshare.5104873.v1특허: US05246961uspto-grants-1993_09