2-(N-tert-butoxycarbonyl)-(2R,3R,4E)-4-octadene-1,3-diol | 605668-85-7

• 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: 2-(N-tert-butoxycarbonyl)-(2R,3R,4E)-4-octadene-1,3-diol
• 英文别名: tert-butyl (3E,1R,2R)-N-[2-hydroxy-1-(hydroxymethyl)-3-heptadecenyl]-carbamate；(2R,3R,4E)-2-(t-butoxycarbonylamino)octadec-4-en-1,3-diol；tert-butyl ((2R,3R,E)-1,3-dihydroxyoctadec-4-en-2-yl)carbamate；tert-butyl N-[(E,2R,3R)-1,3-dihydroxyoctadec-4-en-2-yl]carbamate
• CAS: 605668-85-7
• 化学式: C₂₃H₄₅NO₄
• 分子量: 399.615
• InChiKey: UMUDVBSIURBUGW-LHEOCQAHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  28
• 可旋转键数：
  18
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  78.8
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(N-tert-butoxycarbonyl)-(2R,3R,4E)-4-octadene-1,3-diol 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以87%的产率得到(2R,3R,4E)-2-氨基-4-十八碳烯-1,3-二醇
  参考文献：
  名称：

  由手性氮丙啶不同地合成非对映体神经鞘氨醇

  摘要：

  从单一中间体手性氮丙啶（2）开始合成了鞘氨醇的所有四个立体异构体，该中间体通过酶促脱对称化以对映体形式有效制备。氮丙啶（2）转化为3，用于合成4。两种先进的关键中间体乙烯基氮丙啶3和4分别成功地转化为苏式鞘氨醇1a和1b。使用Grubbs II催化剂进行的闭环复分解（RCM）是合成中的关键反应。两个赤型鞘氨醇1c和1d通过乙烯基氮丙啶3和4的扩环反应合成，然后进行RCM反应合成。成功的发散性合成证实，手性乙烯基氮丙啶2可用作合成鞘氨醇相关天然产物的关键中间体。

  DOI：

  10.1002/bkcs.10830
• 作为产物：
  描述：

  2-(tert-butoxycarbonylamino)-3-hydroxypropionic acid methyl ester 在 甲醇 、 正丁基锂 、 Amberlyst 15 、 二异丁基氢化铝 、 对甲苯磺酸 、 红铝 作用下， 以 乙醚 、 正己烷 、 甲苯 、 苯 为溶剂， 反应 78.0h， 生成 2-(N-tert-butoxycarbonyl)-(2R,3R,4E)-4-octadene-1,3-diol
  参考文献：
  名称：

  Synthesis of fluorescent lactosylceramide stereoisomers

  摘要：

  The intracellular distribution of synthetic glycosphingolipids (GSLs) bearing a fluorophore can be monitored in living cells by fluorescence microscopy. We reported previously that variation in the length of the long-chain base and in the structure of the carbohydrate-containing polar head group of (2S,3R) (or D-erythro-)-beta-lactosylceramide (LacCer) did not alter the mechanism of endocytic uptake from the plasma membrane of various mammalian cell types [Singh, R.D., Puri, V., Valiyaveettil, J.T., Marks, D.L., Bittman, R., Pagano, R.E., 2003. Selective caveolin-l-dependent endocytosis of glycosphingolipids. Mol. Biol. Cell 14, 3254-3265]. To extend our examination of the molecular features in LacCer that are responsible for its uptake by the caveolar-requiring endocytic pathway, we have synthesized the three unnatural stereoisomers [(2R,3R)-, (2S,3S)-, and (2R,3S)] of dipyrromethene difluoride (BODIPY (TM))-LacCer. These analogues will be used to probe the role of stereochemistry in the long-chain base of LacCer in the mechanism of endocytic uptake. (c) 2006 Elsevier Ireland Ltd. All rights reserved.

  DOI：

  10.1016/j.chemphyslip.2006.03.001

文献信息

• Studies on the inhibition of sphingosine-1-phosphate lyase by stabilized reaction intermediates and stereodefined azido phosphates
  作者：Pol Sanllehí、José-Luís Abad、Jordi Bujons、Josefina Casas、Antonio Delgado

  DOI：10.1016/j.ejmech.2016.08.008

  日期：2016.11

  te lyase have been designed and tested on the bacterial (StS1PL) and the human (hS1PL) enzymes. Amino phosphates 1, 12, and 32, mimicking the intermediate aldimines of the catalytic process, were weak inhibitors on both enzyme sources. On the other hand, a series of stereodefined azido phosphates, resulting from the replacement of the amino group of the natural substrates with an azido group, afforded

  已经设计了两种PLP依赖性酶鞘氨醇-1-磷酸裂解酶抑制剂，并在细菌（StS1PL）和人（hS1PL）酶上进行了测试。氨基磷酸盐1，12，和32，模仿催化过程的中间醛亚胺，分别在两个酶来源弱抑制剂。另一方面，通过用叠氮基团取代天然底物的氨基而产生的一系列立体定义的叠氮基磷酸酯，在两种酶源上均提供了低微摩尔范围内的竞争性抑制剂。这种相似的行为代表了两种酶在其活性位点水平上报道的结构相似性的实验证据。有趣的是，反-非天然对映异构体系列的异构体，是hS1PL上最有效的抑制剂。
• Syntheses of sphingosine-1-phosphate stereoisomers and analogues and Their interaction with EDG receptors
  作者：Hyun-Suk Lim、Yong-Seok Oh、Pann-Ghill Suh、Sung-Kee Chung

  DOI：10.1016/s0960-894x(02)00893-4

  日期：2003.1

  Sphingosine-1-phosphate (S1P) is considered to be an important regulator of diverse biological processes acting as a natural ligand to EDG receptors. As a preliminary study to develop potent and selective agonist and antagonist for EDG receptors, we report synthesis of S1P stereoisomers and analogues and their binding affinities to EDG-1, -3, and -5. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Novel, efficient and stereospecific synthesis of xylo-(2R,3S,4S)-phytosphingosine and threo-(2R,3R)-sphingosine
  作者：Sadagopan Raghavan、A. Rajender、J.S. Yadav

  DOI：10.1016/s0957-4166(03)00427-0

  日期：2003.7

  The stereo- and regioselective elaboration of a bromohydrin from an olefinic precursor and Pummerer ene reaction for carbon-carbon bond formation are the key steps in a novel and flexible synthesis of xylo-phytosphingosine and threo-sphingosine. (C) 2003 Elsevier Ltd. All rights reserved.
• Synthesis of penaresidin derivatives and its biological activity
  作者：Kengo Ohshita、Haruaki Ishiyama、Yohei Takahashi、Junji Ito、Yuzuru Mikami、Jun’ichi Kobayashi

  DOI：10.1016/j.bmc.2007.04.049

  日期：2007.7

  A series of stereoisomers for the azetidine ring of penaresidin B was synthesized and their cytotoxic and antimicrobial activities were evaluated. Among six synthetic isomers 1-6, isomers 4 and 5 showed relatively potent cytotoxic activity against A549 (lung) and HT29 (colon) tumor cells as well as antibacterial activity. (c) 2007 Elsevier Ltd. All rights reserved.
• Divergent Synthesis of Diastereomeric Sphingosines from a Chiral Aziridine
  作者：On-Yu Kang、Mi-Ri Shin、Han-Young Kang

  DOI：10.1002/bkcs.10830

  日期：2016.7

  an enatiopure form. Aziridine (2) was converted to 3, which was used for the synthesis of 4. Both the advanced key intermediates, vinylaziridines 3 and 4, were successfully converted to threo‐sphingosines 1a and 1b, respectively. Ring‐closing metathesis (RCM) using the Grubbs II catalyst was the key reaction in the synthesis. Two erythro‐sphingosines 1c and 1d were synthesized by the ring‐expansion reactions

  从单一中间体手性氮丙啶（2）开始合成了鞘氨醇的所有四个立体异构体，该中间体通过酶促脱对称化以对映体形式有效制备。氮丙啶（2）转化为3，用于合成4。两种先进的关键中间体乙烯基氮丙啶3和4分别成功地转化为苏式鞘氨醇1a和1b。使用Grubbs II催化剂进行的闭环复分解（RCM）是合成中的关键反应。两个赤型鞘氨醇1c和1d通过乙烯基氮丙啶3和4的扩环反应合成，然后进行RCM反应合成。成功的发散性合成证实，手性乙烯基氮丙啶2可用作合成鞘氨醇相关天然产物的关键中间体。