(2R,3R,4S)-2-benzyl-3-(tert-butyldimethylsilanyloxy)-4-hydroxypentanoic acid benzyl ester | 210300-08-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2R,3R,4S)-2-benzyl-3-(tert-butyldimethylsilanyloxy)-4-hydroxypentanoic acid benzyl ester
• 英文别名: benzyl (2R,3R,4S)-2-benzyl-3-[tert-butyl(dimethyl)silyl]oxy-4-hydroxypentanoate
• CAS: 210300-08-6
• 化学式: C₂₅H₃₆O₄Si
• 分子量: 428.644
• InChiKey: HWYSMQIAHWNUTL-PMOQBDJRSA-N

物化性质

• 沸点：
  504.8±50.0 °C(Predicted)
• 密度：
  1.048±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.36
• 重原子数：
  30
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2R,3R,4S)-2-benzyl-3-(tert-butyldimethylsilanyloxy)-4-hydroxypentanoic acid benzyl ester 在 palladium hydroxide - carbon 吡啶 、 4-二甲氨基吡啶 、 偶氮二甲酸二异丙酯 、 氢气 、 氟化氢吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三苯基膦 、 三氟乙酸 作用下， 以 吡啶 为溶剂， 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：

  (2R,3R,4S)-2-benzyl-3-hydroxy-4-(4-methoxybenzyloxy)-pentanoic acid benzyl ester 在 咪唑 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 水 为溶剂， 生成 (2R,3R,4S)-2-benzyl-3-(tert-butyldimethylsilanyloxy)-4-hydroxypentanoic acid benzyl 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

文献信息

• Total synthesis of splenocin B, a potent inhibitor of the pro-inflammatory cytokine from marine-derived Streptomyces sp.
  作者：Ken-ichi Yoshida、Minako Ijiri、Hideo Iio、Yoshinosuke Usuki

  DOI：10.1016/j.tet.2015.10.075

  日期：2015.12

  The first total synthesis of splenocin B (1), a new potent anti-inflammatory antimycin-class antibiotic, has been described. The synthesis of 1 has been accomplished in 8 linear steps, starting from commercially available N-Boc-L-threonine benzyl ester 4 and 3,4-dihydroxypentanoic acid derivative 2. Kita–Trost lactonization via an ethoxyvinyl ester intermediate was utilized for the construction of

  已经描述了脾脏B（1）的第一个全合成，一种新的有效的抗炎抗霉素类抗生素。1的合成已从市售N -Boc-L-苏氨酸苄酯4和3,4-二羟基戊酸衍生物2开始，以8个线性步骤完成。通过乙氧基乙烯基酯中间体进行的Kita-Trost内酯化被用于构建9元双内酯核。
• Total synthesis of the antifungal dilactones UK-2A and UK-3A: The determination of their relative and absolute configurations, analog synthesis and antifungal activities
  作者：Masanao Shimano、Noriyuki Kamei、Tetsuo Shibata、Kiyoshi Inoguchi、Nobuko Itoh、Takashi Ikari、Hisato Senda

  DOI：10.1016/s0040-4020(98)00777-7

  日期：1998.10

  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.
• 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.