tert-butyl (4R,5S)-5-[(2S)-but-3-en-2-yl]-2,2,4-trimethyl-1,3-oxazolidine-3-carboxylate | 368447-29-4

• 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: tert-butyl (4R,5S)-5-[(2S)-but-3-en-2-yl]-2,2,4-trimethyl-1,3-oxazolidine-3-carboxylate
• CAS: 368447-29-4
• 化学式: C₁₅H₂₇NO₃
• 分子量: 269.384
• InChiKey: BACKAXADFPEBFH-TUAOUCFPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 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：

  tert-butyl (4R,5S)-5-[(2S)-but-3-en-2-yl]-2,2,4-trimethyl-1,3-oxazolidine-3-carboxylate 在 2,6-二甲基吡啶 、 正丁基锂 、 potassium tert-butylate 、 臭氧 作用下， 以 二氯甲烷 为溶剂， 反应 149.0h， 生成 (2R,3R,4S,5S,6R)-(+)-6-(tert-butoxycarbonylamino)-3-[(tert-butyldimethylsilyl)oxy]-2,4-dimethyl-5-hydroxyheptanal N,O-acetonide
  参考文献：
  名称：

  Studies towards the synthesis of superstolide A. Synthesis and stereochemical assignment of the C(21)C(26) fragment of superstolide A

  摘要：

  An asymmetric synthesis of the C(21) C(26) fragment of superstolide A is described. A fragment, corresponding to a reductive ozonolysis product of superstolide, as also prepared. Comparison of spectroscopic and optical properties of the corresponding fragment obtained by degraduation of natural superstolide A allowed the confirmation of the stereochemistry of the natural product. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00281-6
• 作为产物：
  描述：

  (R)-2-(叔丁氧羰基氨基)丙醛 在 正丁基锂 、 potassium tert-butylate 、 对甲苯磺酸 作用下， 反应 18.0h， 生成 tert-butyl (4R,5S)-5-[(2S)-but-3-en-2-yl]-2,2,4-trimethyl-1,3-oxazolidine-3-carboxylate
  参考文献：
  名称：

  Studies towards the synthesis of superstolide A. Synthesis and stereochemical assignment of the C(21)C(26) fragment of superstolide A

  摘要：

  An asymmetric synthesis of the C(21) C(26) fragment of superstolide A is described. A fragment, corresponding to a reductive ozonolysis product of superstolide, as also prepared. Comparison of spectroscopic and optical properties of the corresponding fragment obtained by degraduation of natural superstolide A allowed the confirmation of the stereochemistry of the natural product. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00281-6

文献信息

• Insights into the structure–activity relationship of the anticancer compound ZJ-101, a derivative of marine natural product superstolide A: A role played by the lactone moiety
  作者：Haibo Qiu、Shan Qian、Sarah A. Head、Jun O. Liu、Zhendong Jin

  DOI：10.1016/j.bmcl.2016.08.046

  日期：2016.10

  Compound ZJ-101, a structurally simplified analog of the marine natural product superstolide A, was previously developed in our laboratory. In the subsequent structure-activity relationship study, a new analog ZJ-109 was designed and synthesized to probe the importance of the lactone moiety of the molecule by replacing the lactone in ZJ-101 with a lactam. The biological evaluation showed that ZJ-109

  化合物ZJ-101是海洋天然产物超杀菌素A的结构简化类似物，以前是在我们的实验室中开发的。在随后的结构-活性关系研究中，设计并合成了新的类似物ZJ-109，以通过用内酰胺替代ZJ-101中的内酯来探测分子内酯部分的重要性。生物学评估表明，ZJ-109在体外对癌细胞的活性比ZJ-101低约8-12倍，这表明该分子的内酯部分对其抗癌活性很重要。
• Studies towards the synthesis of superstolide A. Synthesis and stereochemical assignment of the C(21)C(26) fragment of superstolide A
  作者：Angela Zampella、Maria Valeria D'Auria

  DOI：10.1016/s0957-4166(01)00281-6

  日期：2001.7

  An asymmetric synthesis of the C(21) C(26) fragment of superstolide A is described. A fragment, corresponding to a reductive ozonolysis product of superstolide, as also prepared. Comparison of spectroscopic and optical properties of the corresponding fragment obtained by degraduation of natural superstolide A allowed the confirmation of the stereochemistry of the natural product. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Yakelis, Neal A.; Roush, William R., Journal of Organic Chemistry, 2003, vol. 68, # 10, p. 3838 - 3843
  作者：Yakelis, Neal A.、Roush, William R.

  DOI：——

  日期：——