(4R)-3-[(Z)-1-dibutylboranyloxyprop-1-enyl]-4-propan-2-yl-1,3-oxazolidin-2-one | 149885-19-8

• 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)-3-[(Z)-1-dibutylboranyloxyprop-1-enyl]-4-propan-2-yl-1,3-oxazolidin-2-one
• CAS: 149885-19-8
• 化学式: C₁₇H₃₂BNO₃
• 分子量: 309.257
• InChiKey: ADCSFLLUNDWXDD-CRNMQVKPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.93
• 重原子数：
  22
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4R)-3-[(Z)-1-dibutylboranyloxyprop-1-enyl]-4-propan-2-yl-1,3-oxazolidin-2-one 、 (S)-(+)-2,4-dimethylpent-4-enal 生成 (4R)-3-[(2S,3R,4S)-3-hydroxy-2,4,6-trimethylhept-6-enoyl]-4-propan-2-yl-1,3-oxazolidin-2-one
  参考文献：
  名称：

  EVANS, D. A.;BARTROLI, J., TETRAHEDRON LETT., 1982, 23, N 8, 807-810

  摘要：

  DOI：
• 作为产物：
  描述：

  三氟甲磺酸二丁硼 、 (R)-(-)-4-异丙基-3-丙酰基-2-恶唑烷酮 在 三乙胺 作用下， 生成 (4R)-3-[(Z)-1-dibutylboranyloxyprop-1-enyl]-4-propan-2-yl-1,3-oxazolidin-2-one
  参考文献：
  名称：

  Towards polyketide libraries — II: Synthesis of chiral aracemic di- and triketides on a solid support

  摘要：

  A new fluoride ion cleavable linker serves as starter unit for iterative asymmetric aldol reactions on a solid support. The synthetic protocol relies on the baron enolate chemistry of D. A. Evens and a cyclic reestablishment of key functionalities. It entails the opportunity for the generation of di-and triketide libraries. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)00924-1

文献信息

• A versatile, synthesis of β-amino acids using the Nicholas reaction. I. Application to β-lactams of the carbapenem class
  作者：Peter A. Jacobi、Wanjun Zheng

  DOI：10.1016/s0040-4039(00)77630-1

  日期：1993.4

  Homochiral acetylenic acids of general structure 10, prepared using the Schreiber modification of the Nicholas reaction, have been converted to β-amino acid derivatives of type 11 by a two steps sequence involving Curtius rearrangement followed by oxidative cleavage of the acetylenic bond. Amino acid derivatives 11 are excellent precursors for β-lactams of the carbapenem class.

  使用尼古拉斯反应的施莱伯修饰法制备的具有一般结构10的同型手性乙炔酸已通过涉及Curtius重排然后乙炔键的氧化裂解的两个步骤序列转化为11型β-氨基酸衍生物。氨基酸衍生物11是碳青霉烯类β-内酰胺的极好的前体。
• Formal Total Syntheses of the β-Lactam Antibiotics Thienamycin and PS-5
  作者：Peter A. Jacobi、Shaun Murphree、Frederic Rupprecht、Wanjun Zheng

  DOI：10.1021/jo952092u

  日期：1996.1.1

  Chiral nonracemic acetylenic acids of general structure 11, prepared using the Schreiber modification of the Nicholas reaction, have been converted to beta-amino acid derivatives of type 12 by a two-step sequence involving Curtius rearrangement followed by oxidative cleavage of the acetylenic bond. Amino acid derivatives 12 are excellent precursors for beta-lactams of the carbapenem class, including the important antibiotics thienamycin (1) and PS-5 (4).
• Asymmetric Aldol Reactions on a Soluble Polymeric Support
  作者：M. Reggelin、V. Brenig、C. Zur

  DOI：10.1021/ol991383c

  日期：2000.2.1

  [GRAPHICS]The combinatorial synthesis of small, nonpeptidic compounds is of increasing interest in current medicinal chemistry. To meet this demand, efficient entries, preferentially on polymeric supports, to pharmacologically interesting classes of compounds such as polyketides are necessary, Therefore, we have developed a synthetic protocol allowing for the asymmetric synthesis of diketides on the soluble support MeOPEG-5000. The strategy employed mainly allows for repeated aldolizations, thus providing access to functionalized polyketides of varying degree of oligomerization.