isobutyric acid (3S,6S,7R,8R)-8-benzyl-3-(2-hydroxy-3-methoxybenzoylamino)-6-methyl-4,9-dioxo-[1,5]dioxonane-7-yl ester

• 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: isobutyric acid (3S,6S,7R,8R)-8-benzyl-3-(2-hydroxy-3-methoxybenzoylamino)-6-methyl-4,9-dioxo-[1,5]dioxonane-7-yl ester
• 英文别名: [(3S,6S,7R,8R)-8-benzyl-3-[(2-hydroxy-3-methoxybenzoyl)amino]-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl] 2-methylpropanoate
• 化学式: C₂₇H₃₁NO₉
• 分子量: 513.544
• InChiKey: QDNHGWAWNIHWKH-BOWONNERSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  37
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  138
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为产物：
  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 N-甲基吗啉 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三氟乙酸 作用下， 以 吡啶 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 17.5h， 生成 isobutyric acid (3S,6S,7R,8R)-8-benzyl-3-(2-hydroxy-3-methoxybenzoylamino)-6-methyl-4,9-dioxo-[1,5]dioxonane-7-yl 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

• SYNTHESIS AND USE OF ISOTOPICALLY LABELED MACROCYCLIC COMPOUNDS
  申请人：DOW AGROSCIENCES LLC

  公开号：US20140186873A1

  公开（公告）日：2014-07-03

  Disclosed herein are isotopically labeled antifungal antibiotics and related compounds. Also disclosed are methods for synthesizing these isotopically labeled molecules and using the same to study the distribution of these compounds in the biosphere as well as the products formed by the breakdown of these isotopically labeled compounds.

  本文披露了同位素标记的抗真菌抗生素和相关化合物。还披露了合成这些同位素标记分子的方法，并利用它们研究这些化合物在生物圈中的分布，以及这些同位素标记化合物降解产生的产物。
• US9482661B2
  申请人：——

  公开号：US9482661B2

  公开（公告）日：2016-11-01