(S)-benzyl 2-((2R,3S,4S)-3,4-dihydroxy-5-oxotetrahydrofuran-2-yl)pyrrolidine-1-carboxylate | 1404101-23-0

• 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: (S)-benzyl 2-((2R,3S,4S)-3,4-dihydroxy-5-oxotetrahydrofuran-2-yl)pyrrolidine-1-carboxylate
• CAS: 1404101-23-0
• 化学式: C₁₆H₁₉NO₆
• 分子量: 321.33
• InChiKey: RDIQEKUWWWEMBB-XDQVBPFNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.43
• 重原子数：
  23.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  96.3
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (S)-benzyl 2-((2R,3S,4S)-3,4-dihydroxy-5-oxotetrahydrofuran-2-yl)pyrrolidine-1-carboxylate 在 5%-palladium/activated carbon 、 氢气 、 dimethyl sulfide borane 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 12.0h， 生成 (-)-(6R,7S,8R,8aS)-6,7,8-trihydroxyindolizidine
  参考文献：
  名称：

  Total synthesis of 1-deoxy-7,8a-di-epi-castanospermine and formal synthesis of pumiliotoxin-251D

  摘要：

  A concise and efficient synthesis of (6R,7S,8R,8aS)-6,7,8-trihydroxyindolizidine (1-deoxy-7,8a-di-epi-castanospermine) 2 is described. The synthesis employs cross metathesis in building the key intermediate 9 and is used effectively in constructing indolizidine skeleton for the total synthesis of 1-deoxy-7, 8a-di-epi-castanospermine and also for the bicyclic framework of pumiliotoxin 251D 12,13. The indolizidine skeleton is achieved in one pot sequence of transformations such as deprotection of Cbz group, reduction of double bond, and cyclization. The configurational and conformational structures of compound 10 are unambiguously confirmed by X-ray analysis. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.08.061
• 作为产物：
  描述：

  (2S)-N-苄氧羰基-2-吡咯烷甲醛 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 四氧化锇 、 N-甲基吗啉氧化物 作用下， 以 四氢呋喃 、 水 、 丙酮 、 甲苯 为溶剂， 反应 8.0h， 生成 (S)-benzyl 2-((2R,3S,4S)-3,4-dihydroxy-5-oxotetrahydrofuran-2-yl)pyrrolidine-1-carboxylate
  参考文献：
  名称：

  Total synthesis of 1-deoxy-7,8a-di-epi-castanospermine and formal synthesis of pumiliotoxin-251D

  摘要：

  A concise and efficient synthesis of (6R,7S,8R,8aS)-6,7,8-trihydroxyindolizidine (1-deoxy-7,8a-di-epi-castanospermine) 2 is described. The synthesis employs cross metathesis in building the key intermediate 9 and is used effectively in constructing indolizidine skeleton for the total synthesis of 1-deoxy-7, 8a-di-epi-castanospermine and also for the bicyclic framework of pumiliotoxin 251D 12,13. The indolizidine skeleton is achieved in one pot sequence of transformations such as deprotection of Cbz group, reduction of double bond, and cyclization. The configurational and conformational structures of compound 10 are unambiguously confirmed by X-ray analysis. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.08.061

文献信息

• α,β-Unsaturated Diazoketones as Platforms in the Asymmetric Synthesis of Hydroxylated Alkaloids. Total Synthesis of 1-Deoxy-8,8a-diepicastanospermine and 1,6-Dideoxyepicastanospermine and Formal Synthesis of Pumiliotoxin 251D
  作者：Barbara Bernardim、Vagner D. Pinho、Antonio C. B. Burtoloso

  DOI：10.1021/jo301967w

  日期：2012.11.2

  A versatile and concise approach for the stereoselective synthesis of mono-, di-, and trihydroxylated indolizidines is presented in four to six steps from Cbz-prolinal and a diazophosphonate. The key steps involved a Wolff rearrangement, followed by a stereoselective dihydroxylation/epoxidation reaction, from an α,β-unsaturated diazoketone. The strategy also permits extension to the synthesis of many

  从Cbz-脯氨酸和重氮膦酸酯的四至六个步骤中提出了一种立体选择性合成单羟基，二羟基和三羟基吲哚并吡啶的通用且简洁的方法。关键步骤涉及沃尔夫夫重排，然后是来自α，β-不饱和重氮酮的立体选择性二羟基化/环氧化反应。该策略还允许扩展到许多天然羟基化的吲哚并立定生物碱的合成，如pumiliotoxin 251D的正式合成所证明的。