cis-((3R,4S,5R)-1-phenylhepta-1,6-diene-3,4,5-triyl)tris(oxy)tris(methylene)tribenzene | 948307-73-1

• 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: cis-((3R,4S,5R)-1-phenylhepta-1,6-diene-3,4,5-triyl)tris(oxy)tris(methylene)tribenzene
• 英文别名: [(1Z,3R,4S,5R)-1-phenyl-3,5-bis(phenylmethoxy)hepta-1,6-dien-4-yl]oxymethylbenzene
• CAS: 948307-73-1
• 化学式: C₃₄H₃₄O₃
• 分子量: 490.642
• InChiKey: APDDHQFDYIMUEB-DNGKODARSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  37
• 可旋转键数：
  14
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (2R,3R,4R)-2,3,4-tri-benzyloxy-6-phenylhex-5-en-1-ol 在 草酰氯 、 sodium hexamethyldisilazane 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 2.67h， 生成 trans-((3R,4S,5R)-1-phenylhepta-1,6-diene-3,4,5-triyl)tris(oxy)tris(methylene)tribenzene 、 cis-((3R,4S,5R)-1-phenylhepta-1,6-diene-3,4,5-triyl)tris(oxy)tris(methylene)tribenzene
  参考文献：
  名称：

  Total synthesis of d-fagomine and 6-deoxyfagomine

  摘要：

  Total synthesis of D-fagomine and 6-deoxyfagomine from readily available D-lyxose is described. The key steps included regioselective and diastereoselective amination, hydroboration-oxidation, and Appel reaction. The reaction of 3,4-anti-tribenzyl ether with chlorosulfonyl isocyanate in toluene at 0 degrees C afforded 3,4-anti-amino alcohol, an essential compound for the preparation of D-fagomine and 6-deoxyfagomine, with a high diastereoselectivity (dr=26:1) in 74% yield. The origin of diastereoselectivity can be explained by the neighboring group effect, which leads to retention of the stereochemistry. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.03.046

文献信息

• Total synthesis of d-fagomine and 6-deoxyfagomine
  作者：Im Sook Min、Seung In Kim、Seungmin Hong、In Su Kim、Young Hoon Jung

  DOI：10.1016/j.tet.2013.03.046

  日期：2013.5

  Total synthesis of D-fagomine and 6-deoxyfagomine from readily available D-lyxose is described. The key steps included regioselective and diastereoselective amination, hydroboration-oxidation, and Appel reaction. The reaction of 3,4-anti-tribenzyl ether with chlorosulfonyl isocyanate in toluene at 0 degrees C afforded 3,4-anti-amino alcohol, an essential compound for the preparation of D-fagomine and 6-deoxyfagomine, with a high diastereoselectivity (dr=26:1) in 74% yield. The origin of diastereoselectivity can be explained by the neighboring group effect, which leads to retention of the stereochemistry. (C) 2013 Elsevier Ltd. All rights reserved.