반응 #6139

ord-9094a061a11242d6a707afb2325720a6

반응 방정식

N#Cc1cccc(O)c1
3-hydroxybenzonitrile
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](OC(C)=O)CS[C@H]1Oc1cccc(C#N)c1
expected product
수율 33.3%
CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](OC(C)=O)CS[C@H]1Oc1cccc(C#N)c1
3-cyanophenyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside
수율 33.3%

반응물

N#Cc1cccc(O)c1
3-hydroxybenzonitrile
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

[Ag+].c1c[n-]cn1
silver imidazolate
[Cl-].[Cl-].[Zn+2]
zinc chloride

용매

ClCCl
methylene chloride

반응 조건

상세 조건
See reaction.notes.procedure_details.

후처리

  1. 1
    기타If the procedure described in Preparation LXXXIII

실험 절차

If the procedure described in Preparation LXXXIII is followed starting from 2 g (16.8.10-3 mol) of 3-hydroxybenzonitrile, 2.9 mg (16.5.10-3 mol) of silver imidazolate, 6.5 g (18.3.10-3 mol) of 2,3,4-tri-O-acetyl-5-thio-α-D-xylopyranosyl bromide and 4.6 g (33.6.10-3 mol) of zinc chloride in 80 ml of methylene chloride, 2.2 g (yield: 33%) of the expected product are obtained after purification by chromatography on silica gel using a hexane/ethyl acetate mixture (3/1 v/v) as the eluent, and precipitation in ether.

출처

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