(+)-(4S)-3-<(2'R)-2'-(hydroxymethyl)butanoyl>-4-benzyl-2-oxazolidinone | 150615-45-5

• 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: (+)-(4S)-3-<(2'R)-2'-(hydroxymethyl)butanoyl>-4-benzyl-2-oxazolidinone
• 英文别名: (4S)-4-benzyl-3-[(2R)-2-(hydroxymethyl)butanoyl]oxazolidin-2-one；(4S)-4-benzyl-3-[(2R)-2-(hydroxymethyl)butanoyl]-1,3-oxazolidin-2-one
• CAS: 150615-45-5
• 化学式: C₁₅H₁₉NO₄
• 分子量: 277.32
• InChiKey: UMSNJSYOAXFPAM-OLZOCXBDSA-N

物化性质

• 沸点：
  469.0±28.0 °C(Predicted)
• 密度：
  1.236±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (+)-(4S)-3-<(2'R)-2'-(hydroxymethyl)butanoyl>-4-benzyl-2-oxazolidinone 在 4-二甲氨基吡啶 、 锂硼氢 、 三乙胺 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 水 为溶剂， 反应 10.0h， 生成 (-)-(2S)-2-((tert-Butyldimethylsiloxy)methyl)butan-1-ol
  参考文献：
  名称：

  Asymmetric Total Synthesis of Tacamonine (Pseudovincamone I) via Radical Cyclization

  摘要：

  The radical cyclizations of (+/-)-(E)-3-((2-(bromomethyl)butoxy)carbonyl)prop-2-enoates 11 and 12 and (+/-)-ethyl (E)-3-{N-[2-(bromomethyl)butyl]-N-[2-(3-indolyl)ethyl]carbamoyl} prop-2-enoate (25) were carried out with (TMS)(3)SiH or Bu(3)SnH in the presence of AIBN. (-)-(2S)-2-((tert-Butyldimethylsilyloxy)methyl)butan-1-ol (6), which was prepared by two different methods, was converted into (+)-25. The radical cyclization of(+)-25 produced piperidinone 18 as a diastereomeric mixture, which was transformed into tacamonine (1).

  DOI：

  10.1021/jo00097a037
• 作为产物：
  描述：

  (S)-4-benzyl-3-butyryloxazolidin-2-one 在 palladium on activated charcoal 氢气 、 四氯化钛 、 三乙胺 作用下， 生成 (+)-(4S)-3-<(2'R)-2'-(hydroxymethyl)butanoyl>-4-benzyl-2-oxazolidinone
  参考文献：
  名称：

  拟外消旋合成：使用氟标记策略制备吡啶多菌素和马匹辛的对映异构体的概念和实施

  摘要：

  介绍了准外消旋合成的概念，并通过吡啶多菌素（其绝对构型指定为 R）和麦匹辛的两种对映异构体的合成进行了说明。与外消旋合成一样，准外消旋合成在单一合成序列中提供两种对映异构体；然而，分离标记用于确保准外消旋混合物可以按需分析、分离和识别。不同链长的氟标签用于标记两种对映体起始材料。将所得准对映体混合以制备准外消旋物，然后在合成的连续步骤中将其像真正的外消旋物一样处理。氟色谱法用于将最终的准外消旋物分离或分层为两种组分，然后将其分离以提供（真正的）对映体产品。

  DOI：

  10.1021/ja025606x

文献信息

• Synthesis of Six-Membered Compounds by Environmentally Friendly Cyclization Using Indirect Electrolysis
  作者：Masataka Ihara、Akira Katsumata、Fumihito Setsu、Yuji Tokunaga、Keiichiro Fukumoto

  DOI：10.1021/jo951653e

  日期：1996.1.1

  [Ni(cyclam)](ClO4)(2)-catalyzed indirect electroreduction of olefinic bromides produced six-membered compounds in low to high yields. The synthetic intermediate 49 of Ipecac and Corynanthe alkaloids was obtained in 88% yield in a highly stereoselective manner. Lactam 66, the synthetic precursor of tacamonine, was prepared in 49% yield as a mixture of two diastereoisomers. The electrolysis of the bromoacetates gave the debrominated compounds in good yields.
• Total synthesis of (+)-spiculoic acid A
  作者：Daisuke Matsumura、Takumi Toda、Takashi Hayamizu、Kiyoto Sawamura、Ken-ichi Takao、Kin-ichi Tadano

  DOI：10.1016/j.tetlet.2009.02.101

  日期：2009.7

  The total synthesis of natural (+)-spiculoic acid A, a new cytotoxic marine natural product of polyketide origin, has been accomplished for the first time. The key step of the total synthesis was a stereciselective and high-yielding intramolecular Diels-Alder reaction of a highly functionalized (E,E,E)-2,7,9-dodecanal derivative for the construction of the core tetrahydroindan-2-one skeleton. (C) 2009 Elsevier Ltd. All rights reserved.
• Quasiracemic Synthesis:  Concepts and Implementation with a Fluorous Tagging Strategy to Make Both Enantiomers of Pyridovericin and Mappicine
  作者：Qisheng Zhang、Alexey Rivkin、Dennis P. Curran

  DOI：10.1021/ja025606x

  日期：2002.5.1

  The concept of quasiracemic synthesis is introduced and illustrated with syntheses of both enantiomers of pyridovericin (whose absolute configuration is assigned as R) and mappicine. Like racemic synthesis, quasiracemic synthesis provides both enantiomers in a single synthetic sequence; however, separation tagging is used to ensure that quasiracemic mixtures can be analyzed, separated, and identified

  介绍了准外消旋合成的概念，并通过吡啶多菌素（其绝对构型指定为 R）和麦匹辛的两种对映异构体的合成进行了说明。与外消旋合成一样，准外消旋合成在单一合成序列中提供两种对映异构体；然而，分离标记用于确保准外消旋混合物可以按需分析、分离和识别。不同链长的氟标签用于标记两种对映体起始材料。将所得准对映体混合以制备准外消旋物，然后在合成的连续步骤中将其像真正的外消旋物一样处理。氟色谱法用于将最终的准外消旋物分离或分层为两种组分，然后将其分离以提供（真正的）对映体产品。
• Asymmetric Total Synthesis of Tacamonine (Pseudovincamone I) via Radical Cyclization
  作者：Masataka Ihara、Fumihito Setsu、Miyuki Shohda、Nobuaki Taniguchi、Yuji Tokunaga、Keiichiro Fukumoto

  DOI：10.1021/jo00097a037

  日期：1994.9

  The radical cyclizations of (+/-)-(E)-3-((2-(bromomethyl)butoxy)carbonyl)prop-2-enoates 11 and 12 and (+/-)-ethyl (E)-3-N-[2-(bromomethyl)butyl]-N-[2-(3-indolyl)ethyl]carbamoyl} prop-2-enoate (25) were carried out with (TMS)(3)SiH or Bu(3)SnH in the presence of AIBN. (-)-(2S)-2-((tert-Butyldimethylsilyloxy)methyl)butan-1-ol (6), which was prepared by two different methods, was converted into (+)-25. The radical cyclization of(+)-25 produced piperidinone 18 as a diastereomeric mixture, which was transformed into tacamonine (1).