benzyl (3R,4R,4aR,5S)-5-hydroxy-3-methyl-4-[(2-methylpropan-2-yl)oxycarbonylamino]-1-phenylmethoxycarbonylimino-3,4,4a,5,6,7-hexahydropyrrolo[1,2-c]pyrimidine-2-carboxylate | 1003193-12-1

• 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: benzyl (3R,4R,4aR,5S)-5-hydroxy-3-methyl-4-[(2-methylpropan-2-yl)oxycarbonylamino]-1-phenylmethoxycarbonylimino-3,4,4a,5,6,7-hexahydropyrrolo[1,2-c]pyrimidine-2-carboxylate
• CAS: 1003193-12-1
• 化学式: C₂₉H₃₆N₄O₇
• 分子量: 552.627
• InChiKey: DOXVKXAMBUPUAH-GOUWZUTHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  40
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  130
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  benzyl (3R,4R,4aR,5S)-5-hydroxy-3-methyl-4-[(2-methylpropan-2-yl)oxycarbonylamino]-1-phenylmethoxycarbonylimino-3,4,4a,5,6,7-hexahydropyrrolo[1,2-c]pyrimidine-2-carboxylate 在 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  （-）-脱氨基甲酰氧基萨克毒素的全合成。

  摘要：

  DOI：

  10.1002/anie.200703326
• 作为产物：
  描述：

  benzyl (3R,4R,4aR,5S)-3-methyl-4-[(2-methylpropan-2-yl)oxycarbonylamino]-1-phenylmethoxycarbonylimino-5-tri(propan-2-yl)silyloxy-3,4,4a,5,6,7-hexahydropyrrolo[1,2-c]pyrimidine-2-carboxylate 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 以94%的产率得到benzyl (3R,4R,4aR,5S)-5-hydroxy-3-methyl-4-[(2-methylpropan-2-yl)oxycarbonylamino]-1-phenylmethoxycarbonylimino-3,4,4a,5,6,7-hexahydropyrrolo[1,2-c]pyrimidine-2-carboxylate
  参考文献：
  名称：

  Total Synthesis of (−)- and (+)-Decarbamoyloxysaxitoxin and (+)-Saxitoxin

  摘要：

  AbstractPlaying the sax: The enantioselective total syntheses of (−)‐ and (+)‐decarbamoyloxysaxitoxin (doSTX) and (+)‐saxitoxin (STX) are reported. A new methodology was developed for the synthesis of STXs, featuring discriminative reduction of the nitro group and NO bond in nitroisoxazolidine.magnified imageEnantioselective total syntheses of (−)‐ and (+)‐decarbamoyloxysaxitoxin (doSTX) and (+)‐saxitoxin (STX) were achieved. The characteristic spiro‐fused cyclic guanidine structure of STX was constructed by oxidation at the C4 position with IBX via an α‐iminium carbonyl intermediate and acid‐promoted cyclization of guanidine at the C5 position. A second‐generation methodology was developed for the synthesis of STX, featuring discriminative reduction of the nitro group and NO bond in nitroisoxazolidine. This approach provides efficient access to the key diamine intermediate for STXs.

  DOI：

  10.1002/asia.200800382

文献信息

• Total Synthesis of (−)-Decarbamoyloxysaxitoxin
  作者：Osamu Iwamoto、Hiroyuki Koshino、Daisuke Hashizume、Kazuo Nagasawa

  DOI：10.1002/anie.200703326

  日期：2007.11.19
• Total Synthesis of (−)- and (+)-Decarbamoyloxysaxitoxin and (+)-Saxitoxin
  作者：Osamu Iwamoto、Ryoko Shinohara、Kazuo Nagasawa

  DOI：10.1002/asia.200800382

  日期：2009.2.2

  AbstractPlaying the sax: The enantioselective total syntheses of (−)‐ and (+)‐decarbamoyloxysaxitoxin (doSTX) and (+)‐saxitoxin (STX) are reported. A new methodology was developed for the synthesis of STXs, featuring discriminative reduction of the nitro group and NO bond in nitroisoxazolidine.magnified imageEnantioselective total syntheses of (−)‐ and (+)‐decarbamoyloxysaxitoxin (doSTX) and (+)‐saxitoxin (STX) were achieved. The characteristic spiro‐fused cyclic guanidine structure of STX was constructed by oxidation at the C4 position with IBX via an α‐iminium carbonyl intermediate and acid‐promoted cyclization of guanidine at the C5 position. A second‐generation methodology was developed for the synthesis of STX, featuring discriminative reduction of the nitro group and NO bond in nitroisoxazolidine. This approach provides efficient access to the key diamine intermediate for STXs.