A stereodivergent synthesis of hydroxyethylene dipeptide isostere via highly diastereoselective epoxidation

Lee KW; Choi HW; Lee BH; Choi BS; Chang JH; Kim YK; Lee JH; Heo TH; Nam DH; Shin H

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A stereodivergent synthesis of hydroxyethylene dipeptide isostere via highly diastereoselective epoxidation

机译：通过高度非对映选择性环氧化立体异构合成羟乙烯二肽等排物

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摘要

Epoxidation of delta-amino-beta,-gamma-unsaturated ester with tri-fluoroperacetic acid afforded its epoxide in a highly diastereoselective manner. Subsequent stereodivergent epoxide opening reactions provided synthetic routes towards both the threo and erythro hydroxyethylene peptide isostere.

机译：δ-氨基-β，-γ-不饱和酯与三氟过氧乙酸的环氧化以高度非对映选择性的方式提供了其环氧化物。随后的立体发散性环氧化物开放反应提供了通向苏式和赤式羟基乙烯肽等排体的合成途径。

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来源
《Synlett》 |2005年第20期|共3页
作者
Lee KW; Choi HW; Lee BH; Choi BS; Chang JH; Kim YK; Lee JH; Heo TH; Nam DH; Shin H;
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正文语种 eng
中图分类有机化学;
关键词
hydroxyethylene isostere; diastereoselective epoxidation; stereodivergent; epoxide ring opening; METHYLENE-GAMMA-BUTYROLACTONES; FUNCTIONALIZED AMINO-ACID; STEREOSELECTIVE-SYNTHESIS; STEREOCONTROLLED SYNTHESIS; ENANTIOSELECTIVE SYNTHESIS; PROTEASE INHIBITOR; HOMOALDOL EQUIVALENT; AQUEOUS-SOLUTION; HIV-PROTEASE; CORE UNIT;

机译：羟基亚乙基甾体;非对映选择性环氧化;立体发散性;环氧化物开环;亚甲基-γ-丁内酯;功能化氨基酸;立体选择性合成;立体控制合成;对映选择性合成;蛋白酶抑制剂;固醇;固醇;固醇;

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专利

1. A stereodivergent synthesis of hydroxyethylene dipeptide isostere via highly diastereoselective epoxidation [J] . Lee KW, Choi HW, Lee BH, Synlett . 2005,第20期

机译：通过高度非对映选择性环氧化立体异构合成羟乙烯二肽等排物
2. Diastereoselective synthesis of highly functionalized fluoroalkene dipeptide isosteres and its application to Fmoc-based solid-phase synthesis of a cyclic pentapeptide mimetic [J] . Narumi T, Tomita K, Inokuchi E, Tetrahedron . 2008,第19期

机译：非功能性合成高度官能化的氟烯烃二肽等排物及其在基于Fmoc的固相合成环状五肽模拟物中的应用
3. Asymmetric Synthesis of Chiral Organofluorine Compounds: Use of Nonracemic Fluoroiodoacetic Acid as a Practical Electrophile and Its Application to the Synthesis of Monofluoro Hydroxyethylene Dipeptide Isosteres within a Novel Series of HIV Protease [J] . A.G. myers, J.K. Barbay, B. Zhong Chemtracts . 2001,第14期

机译：手性有机氟化合物的不对称合成：非外消旋氟代碘乙酸作为一种实用的亲电试剂，及其在一系列新型HIV蛋白酶中合成一氟羟基乙烯二肽等排体的应用
4. Efficient diastereoselective synthesis of a hydroxyethylene dipeptide isostere [C] . Satendra Singh, Pius Baur, Michael W.Pennington the International Peptide Symposium . 2001

机译：高效的羟基乙烯二肽虫合成的合成
5. Total synthesis and biological evaluation of fluoroolefin-containing dipeptide isosteres as inhibitors of dipeptidyl peptidase IV (CD26). [D] . Lin, Jian. 1998

机译：作为二肽基肽酶IV（CD26）抑制剂的含氟烯烃的二肽等位基因的全合成和生物学评估。
6. An Efficient Synthesis of Hydroxyethylene Dipeptide Isosteres: The Core Unit of Potent HIV-1 Protease Inhibitors [O] . Arun K. Ghosh, Sean P. McKee, Wayne J. Thompson -1

机译：高效合成羟乙基二肽等排体：强大的HIV-1蛋白酶抑制剂的核心单元。
7. Synthesis of a Tripeptide Derivative Containing the Gln-Arg Hydroxyethylene Dipeptide Isostere [O] . -1

机译：含有Gln-Arg羟乙烯二肽等蹄酮的三肽衍生物的合成

A stereodivergent synthesis of hydroxyethylene dipeptide isostere via highly diastereoselective epoxidation

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