methyl (4R,5S)-4-[2,3-bis(t-butoxycarbonyl)guanidino]-5-[(t-butyldimethylsilyl)oxy]decanoate | 1593758-63-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: methyl (4R,5S)-4-[2,3-bis(t-butoxycarbonyl)guanidino]-5-[(t-butyldimethylsilyl)oxy]decanoate
• CAS: 1593758-63-4
• 化学式: C₂₈H₅₅N₃O₇Si
• 分子量: 573.846
• InChiKey: RLRPVXOCGOGWDB-RTWAWAEBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.68
• 重原子数：
  39.0
• 可旋转键数：
  11.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  124.55
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  methyl (4R,5S)-4-[2,3-bis(t-butoxycarbonyl)guanidino]-5-[(t-butyldimethylsilyl)oxy]decanoate 在 二异丁基氢化铝 作用下， 以 正己烷 、 甲苯 为溶剂， 反应 1.75h， 以57%的产率得到t-butyl [(5S,6R)-2,2,3,3,12,12-hexamethyl-10-oxo-6-(3-oxopropyl)-5-pentyl-4,11-dioxa-7,9-diaza-3-silatridec-8-ylidene]carbamate
  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：

  methyl (2S,3S)-2-amino-3-hydroxyoctanoate 在 2,6-二甲基吡啶 、 palladium on activated carbon 、 氢气 、 二异丁基氢化铝 、 silver nitrate 、 三乙胺 作用下， 以 正己烷 、 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， -78.0~20.0 ℃ 、101.33 kPa 条件下， 反应 40.67h， 生成 methyl (4R,5S)-4-[2,3-bis(t-butoxycarbonyl)guanidino]-5-[(t-butyldimethylsilyl)oxy]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