[(3S,7R,8R,9S)-7-benzyl-8-hydroxy-9-methyl-2,6-dioxo-[1,5]dioxonane-3-yl]-carbamic acid tert-butyl ester | 215798-10-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: [(3S,7R,8R,9S)-7-benzyl-8-hydroxy-9-methyl-2,6-dioxo-[1,5]dioxonane-3-yl]-carbamic acid tert-butyl ester
• 英文别名: [(3S,7R,8R,9S)-7-benzyl-8-hydroxy-9-methyl-2,6-dioxo-[1,5]dioxonan-3-yl]-carbamic acid t-butyl ester；tert-butyl N-[(3S,7R,8R,9S)-7-benzyl-8-hydroxy-9-methyl-2,6-dioxo-1,5-dioxonan-3-yl]carbamate
• CAS: 215798-10-0
• 化学式: C₂₀H₂₇NO₇
• 分子量: 393.437
• InChiKey: ZOEBXBCGEJYSIA-UKMLZYKCSA-N

物化性质

• 沸点：
  634.5±55.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  111
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  [(3S,7R,8R,9S)-7-benzyl-8-hydroxy-9-methyl-2,6-dioxo-[1,5]dioxonane-3-yl]-carbamic acid tert-butyl ester 在 吡啶 、 三氟乙酸 作用下， 生成 isobutyric acid (3S,6S,7R,8R)-3-amino-8-benzyl-6-methyl-4,9-dioxo-[1,5]dioxonane-7-yl ester
  参考文献：
  名称：

  抗真菌双内酯UK-2A的对映选择性全合成：相对构型和绝对构型的确定

  摘要：

  描述了抗真菌双内酯UK-2A的合成。除了为这种有效的抗真菌抗生素提供可行的合成途径外，这还使我们能够确定九元环中相对构型和绝对构型的分配。

  DOI：

  10.1016/s0040-4039(98)00796-5
• 作为产物：
  描述：

  N-叔丁氧羰基-L-丝氨酸 在 palladium dihydroxide 吡啶 、 4-二甲氨基吡啶 、 偶氮二甲酸二异丙酯 、 氢氟酸 、 氢气 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三苯基膦 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 10.0~25.0 ℃ 、405.3 kPa 条件下， 反应 112.0h， 生成 [(3S,7R,8R,9S)-7-benzyl-8-hydroxy-9-methyl-2,6-dioxo-[1,5]dioxonane-3-yl]-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Total synthesis of the antifungal dilactones UK-2A and UK-3A: The determination of their relative and absolute configurations, analog synthesis and antifungal activities

  摘要：

  The synthesis of the antifungal dilactones, UK-2A and UK-3A, is described. In addition to providing a workable synthetic route to these potent antifungal antibiotics, this has allowed us to determine the assignment of the relative and absolute configurations in the nine-membered ring. Furthermore, UK-2A analogs were also synthesized and evaluated their antifungal activities and cytotoxic activities along with UK-2A, (2R, 3R, 4S, 7R)-UK-2A, UK-3A, (2R, 3R, 4S, 7R)-UK-3A, and antimycin A. The structural requirements for the selective cytotoxicity against yeasts and filamentous fungi will also be suggested. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00777-7

文献信息

• Fungicidal heterocyclic aromatic amides and their compositions, methods of use and preparation
  申请人：——

  公开号：US20020177578A1

  公开（公告）日：2002-11-28

  Heterocyclic aromatic amides (HAA) according to Formula I: 1 wherein X 1 -X 4 , M, Z, and A are herein defined. The invention also encompasses hydrates, salts and complexes thereof. These compounds are useful as antifungal agents.

  杂环芳香酰胺（HAA）根据公式I：1，其中X1-X4，M，Z和A在此定义。发明还包括其水合物，盐和配合物。这些化合物可用作抗真菌剂。
• Fungicidal heterocyclic aromatic amides, their compositions and methods of use
  申请人：Dow AgroSciences LLC

  公开号：EP1493733A2

  公开（公告）日：2005-01-05

  The present invention relates to the field of fungicidal compositions and methods. More particularly, the present invention concerns novel fungicidal heterocyclic aromatic amides of following formula I: wherein: represents a 5 membered heterocyclic aromatic ring, and methods involving application of fungicidally effective amounts of such compounds to the locus of a plant pathogen. The present invention also concerns methods useful in the preparation of heterocyclic aromatic amides and their fungicidal compositions.

  本发明涉及杀菌组合物和方法领域。更具体地说，本发明涉及下式 I 的新型杀菌杂环芳香酰胺： 其中 代表 5 个成员的杂环芳香环，以及将杀真菌有效量的此类化合物施用到植物病原体位点的方法。本发明还涉及用于制备杂环芳香酰胺及其杀菌组合物的方法。
• Evaluation of Inhibitory Activities of UK-2A, an Antimycin-Type Antibiotic, and Its Synthetic Analogues against the Production of Anti-inflammatory Cytokine IL-4
  作者：Yoshinosuke Usuki、Saho Ishii、Minako Ijiri、Ken-Ichi Yoshida、Tetsuya Satoh、Satoru Horigome、Izumi Yoshida、Takashi Mishima、Ken-Ichi Fujita

  DOI：10.1021/acs.jnatprod.8b00559

  日期：2018.11.26

  The inhibitory activities of the antimycin-class antibiotics UK-2A, antimycin A, and splenocin B against the production of anti-inflammatory cytokine IL-4, which is related to IgE-mediated allergic responses in rat basophilic leukemia (RBL-2H3) cells, were evaluated. Although antimycin A and splenocin B showed cytotoxicity at concentrations at which IL-4 release from the cells was restricted, UK-2A was found to restrict IL-4 release without cytotoxicity. Three UK-2A analogues (4-6) were then synthesized and assessed. Compound 5 restricted IL-4 release dose-dependently without cytotoxicity, and its effect was more potent than that of UK-2A.
• FUNGICIDAL HETEROCYCLIC AROMATIC AMIDES AND THEIR COMPOSITIONS, METHODS OF USE AND PREPARATION
  申请人：Dow AgroSciences LLC

  公开号：EP1204643B1

  公开（公告）日：2008-06-04
• US6355660B1
  申请人：——

  公开号：US6355660B1

  公开（公告）日：2002-03-12