(2S,3R)-2-(dibenzylamino)octadec-4-yne-1,3-diol

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2S,3R)-2-(dibenzylamino)octadec-4-yne-1,3-diol
• 化学式: C₃₂H₄₇NO₂
• 分子量: 477.731
• InChiKey: YDNCEBTUVAAMED-AJQTZOPKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9
• 重原子数：
  35
• 可旋转键数：
  18
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  43.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S,3R)-2-(dibenzylamino)octadec-4-yne-1,3-diol 在 20% palladium hydroxide-activated charcoal 、 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 18.0h， 以60%的产率得到D-赤式-二氢-D-鞘氨醇
  参考文献：
  名称：

  对映体纯的抗-β-氨基醇的直接立体选择性合成

  摘要：

  对映体纯的抗-β-氨基醇是由衍生自α-氨基酸的光学纯的α-（N，N-二苄基氨基）苄基酯合成的，方法是在-78°C下依次用DIBAL-H还原为醛，然后在原位添加格氏试剂。除了抗-β-氨基醇，抗2 -氨基- 1,3-二醇和抗以良好的收率（60-95％）和优异的立体选择性获得-3-氨基-1,4-二醇的（de> 95％ ）。我们的技术与底物中存在的游离羟基相容。为了证明该方法的多功能性，从适当的步骤分两步合成了spisulosine和sphinganineN，N-二苄基-1-氨基苄基酯的产率分别为42％和45％。

  DOI：

  10.1021/jo500481j
• 作为产物：
  描述：

  N,N-二苯甲基-L-丝氨酸苯甲酯 在 乙基溴化镁 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 为溶剂， 反应 4.5h， 生成 (2S,3R)-2-(dibenzylamino)octadec-4-yne-1,3-diol
  参考文献：
  名称：

  Synthesis and identification of unprecedented selective inhibitors of CK1ε

  摘要：

  A small and structure-biased library of enantiopure anti-beta-amino alcohols was prepared in a straightforward manner by a simplified version of the Reetz protocol. Antiproliferative activity testing against a panel of five human solid tumor cell lines gave GI(50) values in the range 1-20 mu M. The reverse screening by computational methods against 58 proteins involved in cancer pointed to kinases as possible therapeutic target candidates. The experimental determination of the interaction with 456 kinases indicated that the compounds behave as selective CK1 epsilon inhibitors. Our results demonstrate that the lead compound represents the first selective CK1 epsilon inhibitor with proven antiproliferative activity in cancer cell lines. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.03.046

文献信息

• Direct Stereoselective Synthesis of Enantiomerically Pure <i>anti</i>-β-Amino Alcohols
  作者：Gastón Silveira-Dorta、Osvaldo J. Donadel、Víctor S. Martín、José M. Padrón

  DOI：10.1021/jo500481j

  日期：2014.8.1

  Enantiomerically pure anti-β-amino alcohols were synthesized from optically pure α-(N,N-dibenzylamino)benzyl esters, derived from α-amino acids, by the sequential reduction to aldehyde with DIBAL-H at −78 °C and subsequent in situ addition of Grignard reagents. Besides anti-β-amino alcohols, anti-2-amino-1,3-diols and anti-3-amino-1,4-diols were obtained in good yields (60–95%) and excellent stereoselectivity

  对映体纯的抗-β-氨基醇是由衍生自α-氨基酸的光学纯的α-（N，N-二苄基氨基）苄基酯合成的，方法是在-78°C下依次用DIBAL-H还原为醛，然后在原位添加格氏试剂。除了抗-β-氨基醇，抗2 -氨基- 1,3-二醇和抗以良好的收率（60-95％）和优异的立体选择性获得-3-氨基-1,4-二醇的（de> 95％ ）。我们的技术与底物中存在的游离羟基相容。为了证明该方法的多功能性，从适当的步骤分两步合成了spisulosine和sphinganineN，N-二苄基-1-氨基苄基酯的产率分别为42％和45％。
• A facile stereodivergent synthesis of threo- and erythro-N,N-dibenzyl sphingosines from (S)-N,N-dibenzyl-O-TBDMS-serinal
  作者：José M Andrés、Rafael Pedrosa

  DOI：10.1016/s0957-4166(98)00231-6

  日期：1998.7

  The (L)-threo-N,N-dibenzyl sphingosine was prepared in two steps from the serinal derivative 1 by diastereoselective alkenylation with pentadec-l-enyl(ethyl)zinc and deblocking. (D)-erythro-N,N-Dibenzyl sphingosine was also prepared in two steps from 1 by a highly diastereoselective alkynylation with pentadecynyl magnesium bromide and subsequent stereoselective LAH reduction. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Synthesis and identification of unprecedented selective inhibitors of CK1ε
  作者：Gastón Silveira-Dorta、Inês J. Sousa、Miguel X. Fernandes、Victor S. Martín、José M. Padrón

  DOI：10.1016/j.ejmech.2015.03.046

  日期：2015.5

  A small and structure-biased library of enantiopure anti-beta-amino alcohols was prepared in a straightforward manner by a simplified version of the Reetz protocol. Antiproliferative activity testing against a panel of five human solid tumor cell lines gave GI(50) values in the range 1-20 mu M. The reverse screening by computational methods against 58 proteins involved in cancer pointed to kinases as possible therapeutic target candidates. The experimental determination of the interaction with 456 kinases indicated that the compounds behave as selective CK1 epsilon inhibitors. Our results demonstrate that the lead compound represents the first selective CK1 epsilon inhibitor with proven antiproliferative activity in cancer cell lines. (C) 2015 Elsevier Masson SAS. All rights reserved.