반응 #6140

ord-de6b93c29d3a4007a7f8a9a45c1c7379

반응 방정식

CC(=O)O[C@H]1[C@H](OC(C)=O)CSC(Br)[C@@H]1OC(C)=O
2,3,4-tri-O-acetyl-5-thio-D-xylopyranosyl bromide
N#Cc1cccc(O)c1
3-hydroxybenzonitrile
→
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 25.0%
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 25.0%

반응물

CC(=O)O[C@H]1[C@H](OC(C)=O)CSC(Br)[C@@H]1OC(C)=O
2,3,4-tri-O-acetyl-5-thio-D-xylopyranosyl bromide
N#Cc1cccc(O)c1
3-hydroxybenzonitrile

시약

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

용매

CC#N
acetonitrile
Cc1ccccc1
toluene

반응 조건

상세 조건
See reaction.notes.procedure_details.

후처리

  1. 1
    기타If the procedure described in Preparation LXXVIII

실험 절차

If the procedure described in Preparation LXXVIII is followed starting from 0.5 g (1.4.10-3 mol) of 2,3,4-tri-O-acetyl-5-thio-D-xylopyranosyl bromide, 0.25 g (2.1.10-3 mol) of 3-hydroxybenzonitrile and 170 mg (2.1.10-3 mol) of zinc oxide (ZnO) in 4 ml of anhydrous toluene and 4 ml of acetonitrile, 138 mg (yield: 25%) of the expected product are obtained after purification by chromatography on silica gel using a hexane/ethyl acetate mixture (2/1 v/v) as the eluent, and precipitation in ether.

출처

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