(4R,5S)-3-{(2R)-2-[(1S)-3-(tert-butyldimethylsilanyloxy)-1-hydroxypropyl]but-3-enoyl}-4-methyl-5-phenyloxazolidin-2-one | 299204-04-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (4R,5S)-3-{(2R)-2-[(1S)-3-(tert-butyldimethylsilanyloxy)-1-hydroxypropyl]but-3-enoyl}-4-methyl-5-phenyloxazolidin-2-one
• 英文别名: (4R,5S)-3-[(2R,3S)-5-[tert-butyl(dimethyl)silyl]oxy-2-ethenyl-3-hydroxypentanoyl]-4-methyl-5-phenyl-1,3-oxazolidin-2-one
• CAS: 299204-04-9
• 化学式: C₂₃H₃₅NO₅Si
• 分子量: 433.62
• InChiKey: GLQQBEFHEKMOJA-RSPOEFSDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.67
• 重原子数：
  30
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  76.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (4R,5S)-3-{(2R)-2-[(1S)-3-(tert-butyldimethylsilanyloxy)-1-hydroxypropyl]but-3-enoyl}-4-methyl-5-phenyloxazolidin-2-one 在 吡啶 、 sodium tetrahydroborate 、 三丁基硼 、 溶剂黄146 作用下， 以 四氢呋喃 、 二甲基亚砜 为溶剂， 反应 7.5h， 生成 (3S,4R)-1-[(tert-butyldimethylsilyl)oxy]-4-methylhex-5-en-3-ol
  参考文献：
  名称：

  Synthesis of 15,20-triamide analogue with polar substituent on the phenyl ring of arenastatin A, an extremely potent cytotoxic spongean depsipeptide

  摘要：

  In order to increase metabolic stability and water solubility of arenastatin A, an extremely potent cytotoxic depsipeptide from the Okinawan marine sponge of Dysidea arenaria, several 15,20-triamide analogues with a polar substituent on the phenyl ring were synthesized. The 15,20-triamide analogues with a polar substituent (24, 30, and 31) showed increased solubility to MeOH and stronger cytotoxicity against KB cells in comparison with the parental 15,20-triamide analogue (2). Furthermore, the diethylamine analogue (30) exhibited in vivo anti-tumor activity against subcutaneously implanted murine sarcoma. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.07.019
• 作为产物：
  描述：

  (4R,5S)-3-[(2E)-2-丁烯酰]-4-甲基-5-苯基-1,3-恶唑烷-2-酮 在 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 (4R,5S)-3-{(2R)-2-[(1S)-3-(tert-butyldimethylsilanyloxy)-1-hydroxypropyl]but-3-enoyl}-4-methyl-5-phenyloxazolidin-2-one
  参考文献：
  名称：

  Synthesis of 15,20-triamide analogue with polar substituent on the phenyl ring of arenastatin A, an extremely potent cytotoxic spongean depsipeptide

  摘要：

  In order to increase metabolic stability and water solubility of arenastatin A, an extremely potent cytotoxic depsipeptide from the Okinawan marine sponge of Dysidea arenaria, several 15,20-triamide analogues with a polar substituent on the phenyl ring were synthesized. The 15,20-triamide analogues with a polar substituent (24, 30, and 31) showed increased solubility to MeOH and stronger cytotoxicity against KB cells in comparison with the parental 15,20-triamide analogue (2). Furthermore, the diethylamine analogue (30) exhibited in vivo anti-tumor activity against subcutaneously implanted murine sarcoma. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.07.019

文献信息

• Synthesis and Biophysical Studies on 35-Deoxy Amphotericin B Methyl Ester
  作者：Alex M. Szpilman、Damiano M. Cereghetti、Jeffrey M. Manthorpe、Nicholas R. Wurtz、Erick M. Carreira

  DOI：10.1002/chem.200900231

  日期：2009.7.20

  amphotericin B is presented. A modular strategy for the synthesis of amphotericin B and its designed analogues is developed, which relies on an efficient gram‐scale synthesis of various subunits of amphotericin B. A novel method for the coupling of the mycosamine to the aglycone was identified. The implementation of the approach has enabled the preparation of 35‐deoxy amphotericin B methyl ester. Investigation

  介绍了分子编辑在阐明两性霉素B作用机理中的用途。开发了一种用于合成两性霉素B及其设计类似物的模块化策略，该策略依赖于两性霉素B各种亚基的有效克级合成。鉴定了一种将霉菌胺与糖苷配基偶联的新方法。该方法的实施使得能够制备35-脱氧两性霉素B甲酯。对这种两性霉素B同源物的抗真菌活性和外排诱导能力的研究为35-羟基的作用提供了新线索，并且与双桶离子通道参与引起电解质外排的现象是一致的。
• Synthesis of 35-Deoxy Amphotericin B Methyl Ester: A Strategy for Molecular Editing
  作者：Alex M. Szpilman、Damiano M. Cereghetti、Nicholas R. Wurtz、Jeffrey M. Manthorpe、Erick M. Carreira

  DOI：10.1002/anie.200800589

  日期：2008.5.26
• Convergent assembly of aldol linkages. A study of the stereoselective nitrile oxide cycloaddition reaction
  作者：Glenn J McGarvey、Jeffrey A Mathys、Kenneth J Wilson

  DOI：10.1016/s0040-4039(00)00981-3

  日期：2000.8

  The aldol equivalency of a stereoselective nitrile oxide cycloaddition is exploited in the development of a general synthetic strategy to the polyene macrolide antibiotics. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Synthesis of 15,20-triamide analogue with polar substituent on the phenyl ring of arenastatin A, an extremely potent cytotoxic spongean depsipeptide
  作者：Naoyuki Kotoku、Tomoya Kato、Fuminori Narumi、Emiko Ohtani、Sayo Kamada、Shunji Aoki、Naoki Okada、Shinsaku Nakagawa、Motomasa Kobayashi

  DOI：10.1016/j.bmc.2006.07.019

  日期：2006.11

  In order to increase metabolic stability and water solubility of arenastatin A, an extremely potent cytotoxic depsipeptide from the Okinawan marine sponge of Dysidea arenaria, several 15,20-triamide analogues with a polar substituent on the phenyl ring were synthesized. The 15,20-triamide analogues with a polar substituent (24, 30, and 31) showed increased solubility to MeOH and stronger cytotoxicity against KB cells in comparison with the parental 15,20-triamide analogue (2). Furthermore, the diethylamine analogue (30) exhibited in vivo anti-tumor activity against subcutaneously implanted murine sarcoma. (c) 2006 Elsevier Ltd. All rights reserved.