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Synthesis and Isomerization of the 2-Methyl Enal Fragment of Acyclic Precursors to 9,11-Diene Analogs of Epothilones
Russian Journal of Organic Chemistry ( IF 0.8 ) Pub Date : 2020-09-10 , DOI: 10.1134/s1070428020070039
R. F. Valeev , G. R. Sunagatullina , M. S. Miftakhov

Abstract

Yamaguchi esterification of (2Z,5S,6E)-5-(hydroxymethyl)-2,6-dimethyl-7-(2-methyl-1,3-thiazol-4-yl)hepta-2,6-dienal with (2R,5R,6S,7S)-2-(methoxymethoxy)-3,3,5,7-tetramethyl-4-oxo-9-[(1-phenyl-1H-tetrazol-5-yl)sulfonyl-6-[(triethylsilyl)oxy]nonanoic acid afforded the expected acyclic ester. Acid- and base-catalyzed Z,E-isomerization in the 2-methyl enal fragment of acyclic precursors was revealed.



中文翻译:

无环前体的2-甲基烯丙基片段的合成和异构化为上映异构体的9,11-二烯类似物

摘要

(2 Z,5 S,6 E)-5-(羟甲基)-2,6-二甲基-7-(2-甲基-1,3-噻唑-4-基)庚-2,6-二烯的山口酯化反应与(2 R,5 R,6 S,7 S)-2-(甲氧基甲氧基)-3,3,5,7-四甲基-4-氧代-9-[(1-苯基-1 H-四唑-5-基)磺酰基-6-[((三乙基甲硅烷基)氧基]壬酸提供了预期的无环酯。揭示了酸和碱催化的ZE异构化的无环前体的2-甲基烯醛片段中。

更新日期:2020-09-11
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