(S)-4-benzyl-3-{(2'S,3'S,4'R)-3'-hydroxy-4'-[(4-methoxybenzyl)oxy]-2'-methylpentanoyl}oxazolidin-2-one | 1234550-39-0

• 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: (S)-4-benzyl-3-{(2'S,3'S,4'R)-3'-hydroxy-4'-[(4-methoxybenzyl)oxy]-2'-methylpentanoyl}oxazolidin-2-one
• 英文别名: (S)-4-benzyl-3-[(2S,3S,4R)-3-hydroxy-4-(4-methoxybenzyloxy)-2-methylpentanoyl]-1,3-oxazolidin-2-one；(4S)-4-benzyl-3-[(2S,3S,4R)-3-hydroxy-4-[(4-methoxyphenyl)methoxy]-2-methylpentanoyl]-1,3-oxazolidin-2-one
• CAS: 1234550-39-0
• 化学式: C₂₄H₂₉NO₆
• 分子量: 427.497
• InChiKey: DSDBMYAEOZXQTC-AXRVMRSRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  31
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  85.3
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (S)-4-benzyl-3-{(2'S,3'S,4'R)-3'-hydroxy-4'-[(4-methoxybenzyl)oxy]-2'-methylpentanoyl}oxazolidin-2-one 在 2,6-二甲基吡啶 、 三甲基铝 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 19.5h， 生成 (2S,3S,4R)-3-[(tert-butyldimethylsilyl)oxy]-4-(4-methoxybenzyl)oxy-2-methylpentanal
  参考文献：
  名称：

  An architectonic macrolide library based on a C2-symmetric macrodiolide toward pharmaceutical compositions

  摘要：

  A stereodivergent approach to creation of a specific 14-membered macrolide library is described. We designed a new 14-membered macrolide template possessing 10 sterogenic centers, and established a new library of fully-synthesized 14-membered ring compounds. The designed macrodiolides were synthesized through a convergent approach using an Evans aldol reaction, Keck esterification, and Yamaguchi macrolactonization, or Mitsunobu macrolactonization, as key steps. Moreover, introduction of an aminosugar to a macrodiolide aglycone by Schmidt glycosylation also afforded a new macrodiolide. Comparison between the conformation analysis of the macrolides, which we designed, and NMR analysis of the synthetic macrolides, indicated our stereoisomer library has significant diversity. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.01.030
• 作为产物：
  描述：

  (S)-4-苄基-3-丙酰基-2-噁唑烷酮 、 (R)-2-(4-methoxybenzyloxy)propanal 在 三氟甲磺酸二丁硼 、 三乙胺 、 disodium hydrogenphosphate 、 水 、 双氧水 、 柠檬酸 作用下， 以 二氯甲烷 、 甲醇 为溶剂， 反应 2.0h， 以75%的产率得到(S)-4-benzyl-3-{(2'S,3'S,4'R)-3'-hydroxy-4'-[(4-methoxybenzyl)oxy]-2'-methylpentanoyl}oxazolidin-2-one
  参考文献：
  名称：

  新甲霉素和新甲霉素的全合成

  摘要：

  已经实现了新甲霉素和新甲霉素的全合成。这两个大环内酯类含有12元大内酯作为糖苷配基，属于抗生素的间霉素家族，出现在吡咯霉素的生物合成途径中。通过从d -（+）-乳酸甲酯和d开始合成12元大内酯中导致新霉素和新霉素发生结构差异的部分-葡萄糖分别用于新甲氧苄啶和新甲氧苄啶。分别是新甲霉素和新甲霉素的糖苷配基的新甲氧嘧啶和新甲氧嘧啶的合成关键步骤是不对称醛醇缩合反应，山口酯化和使用格鲁布斯第二代催化剂进行的闭环复分解。最后，将戊二烯酮与相应的三氯乙酰亚氨酸酯偶联，然后脱保护，完成了这两种大环内酯类抗生素的总合成。

  DOI：

  10.1016/j.tet.2010.04.039

文献信息

• Total synthesis of neomethymycin and novamethymycin
  作者：Hong-Se Oh、Han-Young Kang

  DOI：10.1016/j.tet.2010.04.039

  日期：2010.6

  d-(+)-lactate and d-glucose, for neomethynolide, and for novamethynolide, respectively. The key steps in synthesis of neomethynolide and novamethynolide, which are aglycones for neomethymycin and novamethymycin, respectively, were asymmetric aldol reactions, Yamaguchi esterification, and ring-closing metathesis using Grubbs’ second generation catalyst. Finally, the coupling of agylcones with the corresponding

  已经实现了新甲霉素和新甲霉素的全合成。这两个大环内酯类含有12元大内酯作为糖苷配基，属于抗生素的间霉素家族，出现在吡咯霉素的生物合成途径中。通过从d -（+）-乳酸甲酯和d开始合成12元大内酯中导致新霉素和新霉素发生结构差异的部分-葡萄糖分别用于新甲氧苄啶和新甲氧苄啶。分别是新甲霉素和新甲霉素的糖苷配基的新甲氧嘧啶和新甲氧嘧啶的合成关键步骤是不对称醛醇缩合反应，山口酯化和使用格鲁布斯第二代催化剂进行的闭环复分解。最后，将戊二烯酮与相应的三氯乙酰亚氨酸酯偶联，然后脱保护，完成了这两种大环内酯类抗生素的总合成。
• An architectonic macrolide library based on a C2-symmetric macrodiolide toward pharmaceutical compositions
  作者：Hayato Nakano、Akihiro Sugawara、Tomoyasu Hirose、Hiroaki Gouda、Shuichi Hirono、Satoshi Ōmura、Toshiaki Sunazuka

  DOI：10.1016/j.tet.2015.01.030

  日期：2015.9

  A stereodivergent approach to creation of a specific 14-membered macrolide library is described. We designed a new 14-membered macrolide template possessing 10 sterogenic centers, and established a new library of fully-synthesized 14-membered ring compounds. The designed macrodiolides were synthesized through a convergent approach using an Evans aldol reaction, Keck esterification, and Yamaguchi macrolactonization, or Mitsunobu macrolactonization, as key steps. Moreover, introduction of an aminosugar to a macrodiolide aglycone by Schmidt glycosylation also afforded a new macrodiolide. Comparison between the conformation analysis of the macrolides, which we designed, and NMR analysis of the synthetic macrolides, indicated our stereoisomer library has significant diversity. (C) 2015 Elsevier Ltd. All rights reserved.