methyl (2S,3S)-2-azido-3-hydroxyoctanoate | 133179-90-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl (2S,3S)-2-azido-3-hydroxyoctanoate
• CAS: 133179-90-5
• 化学式: C₉H₁₇N₃O₃
• 分子量: 215.252
• InChiKey: FFWVCLPFSCVUQB-YUMQZZPRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  15
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  60.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl (2S,3S)-2-azido-3-hydroxyoctanoate 在 2,6-二甲基吡啶 、 20% palladium hydroxide-activated charcoal 、 氢气 、 silver nitrate 、 三乙胺 作用下， 以 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.5h， 生成 methyl (2S,3S)-2-[2,3-bis(t-butoxycarbonyl)guanidino]-3-[(t-butyldimethylsilyl)oxy]octanoate
  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 、 AD-mix-α 、 水 作用下， 以 乙酸乙酯 、 丙酮 、 叔丁醇 为溶剂， 反应 148.5h， 生成 methyl (2S,3S)-2-azido-3-hydroxyoctanoate
  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.