반응 #6135

ord-fe312a64789d4aa28cb765688102371f

반응 방정식

CC(=O)c1cccc(O)c1
1-(3-hydroxyphenyl)ethanone
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
→
CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](OC(C)=O)CS[C@H]1Oc1cccc(C(C)=O)c1
expected product
수율 14.0%
CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](OC(C)=O)CS[C@H]1Oc1cccc(C(C)=O)c1
3-acetylphenyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside
수율 14.0%

반응물

CC(=O)c1cccc(O)c1
1-(3-hydroxyphenyl)ethanone
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

시약

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

용매

CC#N
acetonitrile
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 3.45 g (25.3.10-3 mol) of 1-(3-hydroxyphenyl)ethanone, 6 g (16.9.10-3 mol) of 2,3,4-tri-O-acetyl-5-thio-D-xylopyranosyl bromide, 3 g (17.10-3 mol) of silver imidazolate and 4.6 g (33.7.10-3 mol) of zinc chloride in 90 ml of methylene chloride and 30 ml of acetonitrile, 0.96 g (yield: 14%) of the expected product is obtained after purification by chromatography on silica gel using a toluene/ethyl acetate mixture (6/1 v/v) as the eluent, and crystallization from ether.

출처

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