tert-butyl (5R)-2,2-dimethyl-5-((2S)-2-methyl-6-((R)-6-methyl-1,4-dioxaspiro[4.5]decan-6-yl)-4-oxo-3-(phenylsulfonyl)hexyl)oxazolidine-3-carboxylate | 1613157-56-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: tert-butyl (5R)-2,2-dimethyl-5-((2S)-2-methyl-6-((R)-6-methyl-1,4-dioxaspiro[4.5]decan-6-yl)-4-oxo-3-(phenylsulfonyl)hexyl)oxazolidine-3-carboxylate
• CAS: 1613157-56-4
• 化学式: C₃₂H₄₉NO₈S
• 分子量: 607.809
• InChiKey: NVKOTYAAZAJERC-YPOLYCRLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  42.0
• 可旋转键数：
  9.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  108.44
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  tert-butyl (5R)-2,2-dimethyl-5-((2S)-2-methyl-6-((R)-6-methyl-1,4-dioxaspiro[4.5]decan-6-yl)-4-oxo-3-(phenylsulfonyl)hexyl)oxazolidine-3-carboxylate 在 甲醇 、 disodium hydrogenphosphate 、 5 %sodium amalgam 作用下， 反应 2.0h， 以80%的产率得到tert-butyl (R)-2,2-dimethyl-5-((S)-2-methyl-6-((R)-6-methyl-1,4-dioxaspiro[4.5]decan-6-yl)-4-oxohexyl)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
• 作为产物：
  描述：

  (R)-methyl 3-(6-methyl-1,4-dioxaspiro[4.5]decan-6-yl)propanoate 在 四丙基高钌酸铵 、 二异丁基氢化铝 、 N-甲基吗啉氧化物 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 tert-butyl (5R)-2,2-dimethyl-5-((2S)-2-methyl-6-((R)-6-methyl-1,4-dioxaspiro[4.5]decan-6-yl)-4-oxo-3-(phenylsulfonyl)hexyl)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