(5S,8R)-8-Azido-1,12-bis(benzyloxy)-5-<(methylsulfonyl)oxy>dodecane | 131618-35-4

• 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: (5S,8R)-8-Azido-1,12-bis(benzyloxy)-5-<(methylsulfonyl)oxy>dodecane
• 英文别名: [(5S,8R)-8-azido-1,12-bis(phenylmethoxy)dodecan-5-yl] methanesulfonate
• CAS: 131618-35-4
• 化学式: C₂₇H₃₉N₃O₅S
• 分子量: 517.69
• InChiKey: FICRGLXVVNCSNI-SXOMAYOGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.56
• 重原子数：
  36.0
• 可旋转键数：
  20.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  110.59
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (5S,8R)-8-Azido-1,12-bis(benzyloxy)-5-<(methylsulfonyl)oxy>dodecane 在 palladium on barium sulfate 氢气 作用下， 以 甲醇 为溶剂， 以99%的产率得到(2R,5R)-2,5-Bis<4-(benzyloxy)butyl>pyrrolidine
  参考文献：
  名称：

  Enantioselective total synthesis of (+)- and (-)-pyrrolidine 197B, a new class of alkaloid from the dendrobatid poison frog: assignment of the absolute configuration

  摘要：

  Enantioselective total synthesis of both enantiomers of pyrrolidine 197B (1), a new class of dendrobatid alkaloid, is described. The synthesis begins with the C2 symmetric S,S or R,R diepoxides 4, derived from (S,S)-1,2,5,6-hexanetetraol (2) as a single common chiral synthon, and involves pyrrolidine formation via the cyclic sulfonates to afford (+)- or (-)-1, respectively. The (+) and (-) enantiomers of 1 were converted to the corresponding N-benzoyl derivatives (+)-27 and (-)-27, which were directly compared with 27 derived from natural 1 by HPLC using a Chiralcel column. This comparison established the absolute stereochemistry of the natural enantiomer of pyrrolidine 197B as 2S,5S [(+)-1].

  DOI：

  10.1021/jo00004a011
• 作为产物：
  描述：

  1,2,5,6-二环氧己烷 在 copper(l) iodide 、 sodium azide 作用下， 以 四氢呋喃 、 二甲基亚砜 为溶剂， 反应 1.5h， 生成 (5S,8R)-8-Azido-1,12-bis(benzyloxy)-5-<(methylsulfonyl)oxy>dodecane
  参考文献：
  名称：

  Enantioselective total synthesis of (+)- and (-)-pyrrolidine 197B, a new class of alkaloid from the dendrobatid poison frog: assignment of the absolute configuration

  摘要：

  Enantioselective total synthesis of both enantiomers of pyrrolidine 197B (1), a new class of dendrobatid alkaloid, is described. The synthesis begins with the C2 symmetric S,S or R,R diepoxides 4, derived from (S,S)-1,2,5,6-hexanetetraol (2) as a single common chiral synthon, and involves pyrrolidine formation via the cyclic sulfonates to afford (+)- or (-)-1, respectively. The (+) and (-) enantiomers of 1 were converted to the corresponding N-benzoyl derivatives (+)-27 and (-)-27, which were directly compared with 27 derived from natural 1 by HPLC using a Chiralcel column. This comparison established the absolute stereochemistry of the natural enantiomer of pyrrolidine 197B as 2S,5S [(+)-1].

  DOI：

  10.1021/jo00004a011

文献信息

• MACHINAGA, NOBUO;KIBAYASHI, CHIHIRO, J. ORG. CHEM., 56,(1991) N, C. 1386-1393
  作者：MACHINAGA, NOBUO、KIBAYASHI, CHIHIRO

  DOI：——

  日期：——
• Enantioselective total synthesis of (+)- and (-)-pyrrolidine 197B, a new class of alkaloid from the dendrobatid poison frog: assignment of the absolute configuration
  作者：Nobuo Machinaga、Chihiro Kibayashi

  DOI：10.1021/jo00004a011

  日期：1991.2

  Enantioselective total synthesis of both enantiomers of pyrrolidine 197B (1), a new class of dendrobatid alkaloid, is described. The synthesis begins with the C2 symmetric S,S or R,R diepoxides 4, derived from (S,S)-1,2,5,6-hexanetetraol (2) as a single common chiral synthon, and involves pyrrolidine formation via the cyclic sulfonates to afford (+)- or (-)-1, respectively. The (+) and (-) enantiomers of 1 were converted to the corresponding N-benzoyl derivatives (+)-27 and (-)-27, which were directly compared with 27 derived from natural 1 by HPLC using a Chiralcel column. This comparison established the absolute stereochemistry of the natural enantiomer of pyrrolidine 197B as 2S,5S [(+)-1].