(R)-4-benzyl-3-[(S)-2-(hydroxymethyl)butanoyl]oxazolidin-2-one | 907593-86-6

• 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: (R)-4-benzyl-3-[(S)-2-(hydroxymethyl)butanoyl]oxazolidin-2-one
• 英文别名: (4R)-4-benzyl-3-[(2S)-2-(hydroxymethyl)butanoyl]-1,3-oxazolidin-2-one
• CAS: 907593-86-6
• 化学式: C₁₅H₁₉NO₄
• 分子量: 277.32
• InChiKey: UMSNJSYOAXFPAM-QWHCGFSZSA-N

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：

  (R)-4-benzyl-3-[(S)-2-(hydroxymethyl)butanoyl]oxazolidin-2-one 在 4-二甲氨基吡啶 、 锂硼氢 、 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 反应 8.0h， 生成 ethyl (2E,4R)-4-(tert-butyldimethylsilyloxymethyl)-2-hexenoate
  参考文献：
  名称：

  Directed Orthometalation and the Asymmetric Total Synthesis of N-Deoxymilitarinone A and Torrubiellone B

  摘要：

  A diverted total synthesis (DTS) approach to the total synthesis of pyridone alkaloids N-deoxymilitarinone A (8) and torrubiellone B (10) has been developed. The common intermediate 14 was first assembled by a dual directed orthometalation process using a methoxymethyl group as directed metalation group. Other crucial steps include the assembly of polyenes under aldol condensation for DTS using general and concise strategy and diastereoselective synthesis of the syn-dimethyl array by an Evans aldol reaction.

  DOI：

  10.1021/ol402820d
• 作为产物：
  描述：

  (R)-4-benzyl-3-((S)-2-(benzyloxymethyl)butanoyl)oxazolidin-2-one 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 20.0 ℃ 、506.66 kPa 条件下， 反应 20.0h， 以100%的产率得到(R)-4-benzyl-3-[(S)-2-(hydroxymethyl)butanoyl]oxazolidin-2-one
  参考文献：
  名称：

  Peloruside A 受限类似物合成的收敛策略

  摘要：

  已经证明了一种获取 peloruside A 的不饱和类似物的快速收敛策略。这被描述为 C12-C20 酮片段和带有醛官能团的 C2-C11 吡喃片段之间的原始 C11-C12 醛醇连接，具有高产率和良好的非对映选择性。通过后期闭环复分解反应获得所需的不饱和大环。

  DOI：

  10.1002/ejoc.201201728

文献信息

• 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。
• Convergent Strategy Towards the Synthesis of Restricted Analogues of Peloruside A
  作者：Nicolas Zimmermann、Pierre Pinard、Bertrand Carboni、Pascal Gosselin、Catherine Gaulon-Nourry、Gilles Dujardin、Sylvain Collet、Jacques Lebreton、Monique Mathé-Allainmat

  DOI：10.1002/ejoc.201201728

  日期：2013.4

  A rapid convergent strategy to access unsaturated analogues of peloruside A has been demonstrated. This is depicted as an original C11-C12 aldol connection between a C12-C20 ketone fragment and a C2-C11 pyran fragment bearing an aldehyde function, with high yield and a good level of diastereoselectivity. The desired unsaturated macrocycle was obtained by a late-stage ring closing metathesis reaction

  已经证明了一种获取 peloruside A 的不饱和类似物的快速收敛策略。这被描述为 C12-C20 酮片段和带有醛官能团的 C2-C11 吡喃片段之间的原始 C11-C12 醛醇连接，具有高产率和良好的非对映选择性。通过后期闭环复分解反应获得所需的不饱和大环。
• A stereoselective synthesis of the C11–C19 fragment of (+)-peloruside A
  作者：Zhen-liang Chen、Wei-shan Zhou

  DOI：10.1016/j.tetlet.2006.05.135

  日期：2006.7

  A new route to the synthesis of the C I I-C 19 fragment of peloruside A is described, which includes an aldol reaction with ethyl acetoacetate, P-hydroxyl-directed reduction of P-hydroxy ketone, as well as methylation of C 13 hydroxyl moiety in the system of Mel-Ag2O-MgSO4-CH2Cl2. (c) 2006 Elsevier Ltd. All rights reserved.
• Evans, David A.; Welch, Dennie S.; Speed, Alexander W. H., Journal of the American Chemical Society, 2009, vol. 131, p. 3840 - 3841
  作者：Evans, David A.、Welch, Dennie S.、Speed, Alexander W. H.、Moniz, George A.、Reichelt, Andreas、Ho, Stephen

  DOI：——

  日期：——
• Toward a Total Synthesis of Peloruside A:  Enantioselective Preparation of the C8−C19 Region
  作者：Richard E. Taylor、Meizhong Jin

  DOI：10.1021/ol0358814

  日期：2003.12.1

  [GRAPHICS]An efficient synthetic sequence toward the C8-C19 region of peloruside A has been developed. The route is highlighted by a selective electrophilic cyclization reaction, a single-step epoxide ring-opening/methylation sequence, and a stereoselective Mukaiyama aldol reaction.