tert-butyl (R)-2,2-dimethyl-5-((S)-2-methyl-4-oxobutyl)oxazolidine-3-carboxylate | 756532-88-4

• 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 (R)-2,2-dimethyl-5-((S)-2-methyl-4-oxobutyl)oxazolidine-3-carboxylate
• 英文别名: (R)-tert-butyl 2,2-dimethyl-5-((S)-2-methyl-4-oxobutyl)oxazolidine-3-carboxylate；tert-butyl (5R)-2,2-dimethyl-5-[(2S)-2-methyl-4-oxobutyl]-1,3-oxazolidine-3-carboxylate
• CAS: 756532-88-4
• 化学式: C₁₅H₂₇NO₄
• 分子量: 285.384
• InChiKey: CDCDATRGMFNACP-VXGBXAGGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl (R)-2,2-dimethyl-5-((S)-2-methyl-4-oxobutyl)oxazolidine-3-carboxylate 在 盐酸 、 溶剂黄146 作用下， 以 水 、 乙酸乙酯 为溶剂， 反应 18.5h， 生成 (1R,3S,5S)-3-methyl-8-oxa-6-azabicyclo[3.2.1]octane hydrochloride
  参考文献：
  名称：

  Structure–activity relationships of the truncated norzoanthamines exhibiting collagen protection toward anti-osteoporotic activity

  摘要：

  The marine alkaloid norzoanthamine is a candidate drug for osteoporosis treatment. Due to its structural complexity, simplified analogues possessing similar biological activities are needed for further research. Recently, we found that the bisaminal unit, representing two-thirds of the original structure, is a bioactive equivalent. We synthesized three kinds of further truncated norzoanthamines and evaluated their collagen protection activities. No analog with collagen protection activity comparable to that of the bisaminal unit was found. Thus, we confirmed the importance of the bisaminal unit for the collagen protection activity. Furthermore, we found that the recognition tolerance of the substrate collagen is relatively large by comparing both enantiomers. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.04.040
• 作为产物：
  描述：

  tert-butyl ((2R,4S)-2,5-dihydroxy-4-methylpentyl)carbamate 在 四丙基高钌酸铵 、 sodium hexamethyldisilazane 、 三氧化硫吡啶 、 对甲苯磺酸 、 N-甲基吗啉氧化物 、 三乙胺 、 9-硼双环[3.3.1]壬烷 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 二甲基亚砜 、 丙酮 为溶剂， 反应 11.5h， 生成 tert-butyl (R)-2,2-dimethyl-5-((S)-2-methyl-4-oxobutyl)oxazolidine-3-carboxylate
  参考文献：
  名称：

  Structure–activity relationships of the truncated norzoanthamines exhibiting collagen protection toward anti-osteoporotic activity

  摘要：

  The marine alkaloid norzoanthamine is a candidate drug for osteoporosis treatment. Due to its structural complexity, simplified analogues possessing similar biological activities are needed for further research. Recently, we found that the bisaminal unit, representing two-thirds of the original structure, is a bioactive equivalent. We synthesized three kinds of further truncated norzoanthamines and evaluated their collagen protection activities. No analog with collagen protection activity comparable to that of the bisaminal unit was found. Thus, we confirmed the importance of the bisaminal unit for the collagen protection activity. Furthermore, we found that the recognition tolerance of the substrate collagen is relatively large by comparing both enantiomers. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.04.040

文献信息

• Synthetic Studies of the Zoanthamine Alkaloids: The Total Syntheses of Norzoanthamine and Zoanthamine
  作者：Fumihiko Yoshimura、Minoru Sasaki、Izumi Hattori、Kei Komatsu、Mio Sakai、Keiji Tanino、Masaaki Miyashita

  DOI：10.1002/chem.200900310

  日期：2009.7.6

  Highly effective: We report herein the first and highly efficient total syntheses of norzoanthamine and zoanthamine in full detail, which involves stereoselective synthesis of the requisite triene for an intramolecular Diels–Alder reaction via three‐component coupling reactions, the intramolecular Diels–Alder reaction, and subsequent crucial bis‐aminoacetalization as the key steps.

  高效：我们在此详细报道了去甲乙胺和唑胺的第一个高效的全合成方法，该方法涉及通过三组分偶联反应，分子内Diels-Alder反应，分子内Diels-Alder反应所必需的三烯的立体选择性合成，以及随后的关键双氨基缩醛化为关键步骤。
• Structure–activity relationships of the truncated norzoanthamines exhibiting collagen protection toward anti-osteoporotic activity
  作者：Hironori Inoue、Kazuho Tokita、Seketsu Fukuzawa、Kazuo Tachibana

  DOI：10.1016/j.bmc.2014.04.040

  日期：2014.7

  The marine alkaloid norzoanthamine is a candidate drug for osteoporosis treatment. Due to its structural complexity, simplified analogues possessing similar biological activities are needed for further research. Recently, we found that the bisaminal unit, representing two-thirds of the original structure, is a bioactive equivalent. We synthesized three kinds of further truncated norzoanthamines and evaluated their collagen protection activities. No analog with collagen protection activity comparable to that of the bisaminal unit was found. Thus, we confirmed the importance of the bisaminal unit for the collagen protection activity. Furthermore, we found that the recognition tolerance of the substrate collagen is relatively large by comparing both enantiomers. (C) 2014 Elsevier Ltd. All rights reserved.