4-O-tert-butyl 3-O-methyl (1S,3S,5S)-14-(4-methylphenyl)sulfonyl-7-oxa-4,14-diazatetracyclo[9.4.0.01,5.06,10]pentadeca-6(10),8,11-triene-3,4-dicarboxylate | 1021358-74-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 4-O-tert-butyl 3-O-methyl (1S,3S,5S)-14-(4-methylphenyl)sulfonyl-7-oxa-4,14-diazatetracyclo[9.4.0.01,5.06,10]pentadeca-6(10),8,11-triene-3,4-dicarboxylate
• CAS: 1021358-74-6
• 化学式: C₂₆H₃₀N₂O₇S
• 分子量: 514.599
• InChiKey: PHZCUIKPXOKISJ-UNIVCBNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  36
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  115
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  4-O-tert-butyl 3-O-methyl (1S,3S,5S)-14-(4-methylphenyl)sulfonyl-7-oxa-4,14-diazatetracyclo[9.4.0.01,5.06,10]pentadeca-6(10),8,11-triene-3,4-dicarboxylate 在 dimethyl sulfide borane 、 sodium hydroxide 、 双氧水 作用下， 以 四氢呋喃 、 甲苯 、 水 为溶剂， 反应 1.0h， 以71%的产率得到4-O-tert-butyl 3-O-methyl (1S,3S,5S,11S,12S)-12-hydroxy-14-(4-methylphenyl)sulfonyl-7-oxa-4,14-diazatetracyclo[9.4.0.01,5.06,10]pentadeca-6(10),8-diene-3,4-dicarboxylate
  参考文献：
  名称：

  Expedient Synthesis of the Tetracyclic Core of ent-Nakadomarin A

  摘要：

  An efficient eight-step assembly of the tetracyclic core (ABCD rings) of ent-(+)-nakadomarin A, a bioactive hexacyclic marine alkaloid, has been realized with Sonogashira coupling, platinum(II)-promoted cascade cyclizations, and saturation of a challenging carbon - carbon double bond through a hydroboration/oxidation/xanthate formation/Barton - McCombie deoxygenation sequence as key transformations.

  DOI：

  10.1021/ol800579j
• 作为产物：
  描述：

  1-O-tert-butyl 2-O-methyl (2S)-4-[[3-(furan-3-yl)prop-2-ynyl-(4-methylphenyl)sulfonylamino]methyl]-2,3-dihydropyrrole-1,2-dicarboxylate 在 platinum(II) chloride 作用下， 以 甲苯 为溶剂， 反应 2.5h， 以50%的产率得到4-O-tert-butyl 3-O-methyl (1S,3S,5S)-14-(4-methylphenyl)sulfonyl-7-oxa-4,14-diazatetracyclo[9.4.0.01,5.06,10]pentadeca-6(10),8,11-triene-3,4-dicarboxylate
  参考文献：
  名称：

  Expedient Synthesis of the Tetracyclic Core of ent-Nakadomarin A

  摘要：

  An efficient eight-step assembly of the tetracyclic core (ABCD rings) of ent-(+)-nakadomarin A, a bioactive hexacyclic marine alkaloid, has been realized with Sonogashira coupling, platinum(II)-promoted cascade cyclizations, and saturation of a challenging carbon - carbon double bond through a hydroboration/oxidation/xanthate formation/Barton - McCombie deoxygenation sequence as key transformations.

  DOI：

  10.1021/ol800579j

文献信息

• Expedient Synthesis of the Tetracyclic Core of <i>ent</i>-Nakadomarin A
  作者：Haibing Deng、Xiaobao Yang、Zhaolong Tong、Zhong Li、Hongbin Zhai

  DOI：10.1021/ol800579j

  日期：2008.5.1

  An efficient eight-step assembly of the tetracyclic core (ABCD rings) of ent-(+)-nakadomarin A, a bioactive hexacyclic marine alkaloid, has been realized with Sonogashira coupling, platinum(II)-promoted cascade cyclizations, and saturation of a challenging carbon - carbon double bond through a hydroboration/oxidation/xanthate formation/Barton - McCombie deoxygenation sequence as key transformations.