Diastereoselective synthesis of new O-alkylated and C-branched inositols and their corresponding fluoro analogues

被引:5
|
作者
Collet, Charlotte [1 ,2 ,3 ]
Chretien, Franoise [1 ,2 ]
Chapleur, Yves [1 ,2 ]
Lamande-Langle, Sandrine [1 ,2 ]
机构
[1] Univ Lorraine, F-54500 Vandoeuvre Les Nancy, France
[2] CNRS, UMR 7565, F-54506 Vandoeuvre Les Nancy, France
[3] Nancyclotep, Plateforme Imagerie Mol, F-54500 Vandoeuvre Les Nancy, France
来源
关键词
C-branched; diastereoselective; fluoroinositols; inositols; O-alkylated; AMYLOID-BETA PEPTIDE; SCYLLO-INOSITOL; ALZHEIMERS-DISEASE; GLYCOSYL FLUORIDES; AGGREGATION; CHEMISTRY; PHOSPHATIDYLINOSITOL; STEREOISOMERS; BIOSYNTHESIS; ORIENTATION;
D O I
10.3762/bjoc.12.39
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Efficient routes were developed for the diastereoselective synthesis of new O-alkylated and C-branched inositols and their corresponding fluoro analogues. The key steps of the synthesis were the easy accessibility of different types of arms in term of configuration (myo and scyllo), the linking method and length, which could modulate the biological properties. These inositol derivatives, bearing an arm terminated either with a hydroxy group or a fluorine atom, could be interesting candidates for diastereoisomeric intermediates and biological evaluations, especially for PET imaging experiments.
引用
收藏
页码:353 / 361
页数:9
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共 31 条
  • [1] A NEW METHOD FOR THE SYNTHESIS OF C-BRANCHED CARBOHYDRATES
    KLEMER, A
    BEERMANN, H
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    Mastino, A
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    Iannazzo, D
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    Piperno, A
    Previtera, T
    Rescifina, A
    Romeo, G
    Romeo, R
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