tert-butyl (4S)-5-hydroxy-4-[(1S)-1-(methoxymethoxy)hexyl]-2-[(2-methylpropan-2-yl)oxycarbonylamino]-4,5-dihydroimidazole-1-carboxylate | 1593758-74-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑啉类
• 英文名称: tert-butyl (4S)-5-hydroxy-4-[(1S)-1-(methoxymethoxy)hexyl]-2-[(2-methylpropan-2-yl)oxycarbonylamino]-4,5-dihydroimidazole-1-carboxylate
• CAS: 1593758-74-7
• 化学式: C₂₁H₃₉N₃O₇
• 分子量: 445.557
• InChiKey: AQWNHHWFDCZONM-KSCSMHSMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  31
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  119
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  tert-butyl (4S)-5-hydroxy-4-[(1S)-1-(methoxymethoxy)hexyl]-2-[(2-methylpropan-2-yl)oxycarbonylamino]-4,5-dihydroimidazole-1-carboxylate 在 palladium on activated carbon 、 氢气 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 36.0h， 生成 methyl (4R,5S)-4-[2,3-bis(t-butoxycarbonyl)guanidino]-5-(methoxymethoxy)decanoate
  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
• 作为产物：
  描述：

  反式-2-辛烯甲酯 在 氯化亚砜 、 sodium azide 、 甲基磺酰胺 、 20% palladium hydroxide-activated charcoal 、 AD-mix-α 、 水 、 氢气 、 二异丁基氢化铝 、 silver nitrate 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 正己烷 、 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 丙酮 、 甲苯 、 叔丁醇 为溶剂， -78.0~50.0 ℃ 、101.33 kPa 条件下， 反应 200.08h， 生成 tert-butyl (4S)-5-hydroxy-4-[(1S)-1-(methoxymethoxy)hexyl]-2-[(2-methylpropan-2-yl)oxycarbonylamino]-4,5-dihydroimidazole-1-carboxylate
  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

• 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.