(+)-monanchorin TFA Salt | 1120352-15-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮卓类
• 英文名称: (+)-monanchorin TFA Salt
• 英文别名: (1R,5R,7S)-7-pentyl-6-oxa-2,4-diazabicyclo[3.2.2]non-3-en-3-amine;2,2,2-trifluoroacetic acid
• CAS: 1120352-15-9
• 化学式: C₂HF₃O₂*C₁₁H₂₁N₃O
• 分子量: 325.331
• InChiKey: FJPCSZCESXMPNC-YMQJAAJZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  96.9
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  、 三氟乙酸 以 二氯甲烷 为溶剂， 反应 96.0h， 以130 mg的产率得到(+)-monanchorin TFA Salt
  参考文献：
  名称：

  A New Stereocontrolled Total Synthesis of the Mast Cell Inhibitory Alkaloid, (+)-Monanchorin, via the Wittig Reaction of a Stabilized Ylide with a Cyclic Guanidine Hemiaminal

  摘要：

  An asymmetric total synthesis of the mast cell inhibitor (+)-monanchorin is reported in which a Sharpless AD on 11 and a cyclic sulfate ring opening with an azide feature as key steps. After further manipulation, a novel guanidine-controlled ester reduction provided the guanidine-hemiaminal 25 which underwent Wittig olefination to give 27. Hydrogenation and a second guanidine-controlled reduction of the ester in 28, to obtain aldehyde 29, then set up a trifluoroacetic acid mediated cyclization to give (+)-monanchorin TFA salt.

  DOI：

  10.1021/ol500616v

文献信息

• <i>De Novo</i> Asymmetric Synthesis of (+)-Monanchorin
  作者：Yuzhi Ma、George A. O’Doherty

  DOI：10.1021/acs.orglett.5b02651

  日期：2015.11.6

  A de novo asymmetric total synthesis of the guanidine alkaloid natural product (+)-monanchorin has been achieved in nine steps from the commodity chemicals furan and caproic acid. The asymmetry of the route was introduced by a Noyori reduction of an acylfuran. In addition, this route relies upon an Achmatowicz rearrangement, a diastereoselective palladium catalyzed glycosylation, reductive amination, and an acid catalyzed bicyclic guanidine mixed acetal formation.
• Synthesis of (+)- and (−)-Monanchorin
  作者：Min Yu、Barry B. Snider

  DOI：10.1021/ol802981h

  日期：2009.2.19

  The optically pure epoxy acetal was converted to the protected guanidino alcohol by reaction with NaN3 in DMF, hydrogenation of the azide, and reaction of the amine with MeSC(NBoc)NHBoc, AgNO3, and Et3N. Treatment of the protected guanidino alcohol with 9:1 CDCl3/TFA afforded monanchorin, whose absolute stereochemistry was assigned as shown.
• A New Stereocontrolled Total Synthesis of the Mast Cell Inhibitory Alkaloid, (+)-Monanchorin, via the Wittig Reaction of a Stabilized Ylide with a Cyclic Guanidine Hemiaminal
  作者：Karl J. Hale、Liping Wang

  DOI：10.1021/ol500616v

  日期：2014.4.18

  An asymmetric total synthesis of the mast cell inhibitor (+)-monanchorin is reported in which a Sharpless AD on 11 and a cyclic sulfate ring opening with an azide feature as key steps. After further manipulation, a novel guanidine-controlled ester reduction provided the guanidine-hemiaminal 25 which underwent Wittig olefination to give 27. Hydrogenation and a second guanidine-controlled reduction of the ester in 28, to obtain aldehyde 29, then set up a trifluoroacetic acid mediated cyclization to give (+)-monanchorin TFA salt.