Yb(OTf)3-Catalyzed Desymmetrization of myo-Inositol 1,3,5-Orthoformate and Its Application in the Synthesis of Chiral Inositol Phosphates

被引：7
|
作者：
Padiyar, Laxmansingh T. [1 ]
Zulueta, Medel Manuel L. [1 ]
Sabbavarapu, Narayana Murthy [1 ]
Hung, Shang-Cheng [1 ]
机构：
[1] Acad Sinica, Genom Res Ctr, 128 Sect 2 Acad Rd, Taipei 115, Taiwan
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2017年 / 82卷 / 21期
关键词：
D-MYO-INOSITOL; PHOSPHATIDYLINOSITOL DIMANNOSIDE; ASYMMETRIC PHOSPHORYLATION; DERIVATIVES; PHOSPHORAMIDITE; PATHWAY; 1,3,5-ORTHOBENZOATE; DESYMMETRISATION; POLYPHOSPHATES; ENANTIOMERS;
D O I：
10.1021/acs.joc.7b01919
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A variety of inositol phosphates including myoinositol 1,4,5-trisphosphate, which is a secondary messenger in transmembrane signaling, were selectively synthesized via Yb(OTf)(3)-catalyzed desymmetrization of myo-inositol 1,3,5-orthoformate using a proline-based chiral anhydride as an acylation precursor. The investigated catalytic system could regioselectively differentiate the enantiotopic hydroxy groups of myo-inositol 1,3,5-orthoformate in the presence of a chiral auxiliary. This key step to generate a suitably protected chiral myo-inositol derivatives is described here as a unified approach to access inositol phosphates.
引用
收藏
页码：11418 / 11430
页数：13
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