methyl (2R,3S)-2,3-dihydroxyoctanoate | 1593758-37-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl (2R,3S)-2,3-dihydroxyoctanoate
• 英文别名: methyl syn-2,3-dihydroxyoctanoate
• CAS: 1593758-37-2
• 化学式: C₉H₁₈O₄
• 分子量: 190.24
• InChiKey: FLIBQUYKZOKSLL-JGVFFNPUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  13
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl (2R,3S)-2,3-dihydroxyoctanoate 在 2,6-二甲基吡啶 、 氯化亚砜 、 sodium azide 、 20% palladium hydroxide-activated charcoal 、 水 、 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 、 丙酮 为溶剂， 反应 57.0h， 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 甲基磺酰胺 、 AD-mix-α 作用下， 以 水 、 叔丁醇 为溶剂， 反应 96.0h， 以98%的产率得到methyl (2R,3S)-2,3-dihydroxyoctanoate
  参考文献：
  名称：

  Mammalian blood odorant and chirality: synthesis and sensory evaluation by humans and mice of the racemate and enantiomers of trans-4,5-epoxy-(E)-2-decenal

  摘要：

  The racemate and enantiomers of trans-4,5-epoxy-(E)-2-decenal 1, an odorant with a metallic blood smell, were synthesized. The detection threshold for humans was 0.019 ppb for (2E,4S,5S)-(-)-1 and 0.62 ppb for (2E,4R,5R)-(+)-1, respectively. The racemate (+/-)-1 made mice scared stiff at a dosage of approximately 1 mg, while the enantiomers were not significantly bioactive. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2015.06.011

文献信息

• Mammalian blood odorant and chirality: synthesis and sensory evaluation by humans and mice of the racemate and enantiomers of trans-4,5-epoxy-(E)-2-decenal
  作者：Kenji Mori、Kazumi Osada、Masayasu Amaike

  DOI：10.1016/j.tetasy.2015.06.011

  日期：2015.8

  The racemate and enantiomers of trans-4,5-epoxy-(E)-2-decenal 1, an odorant with a metallic blood smell, were synthesized. The detection threshold for humans was 0.019 ppb for (2E,4S,5S)-(-)-1 and 0.62 ppb for (2E,4R,5R)-(+)-1, respectively. The racemate (+/-)-1 made mice scared stiff at a dosage of approximately 1 mg, while the enantiomers were not significantly bioactive. (C) 2015 Elsevier Ltd. All rights reserved.
• 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.