(2R,3R)-2,3-Epoxypentadecan-1-ol | 165880-19-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 环氧化物
• 英文名称: (2R,3R)-2,3-Epoxypentadecan-1-ol
• 英文别名: ((2R,3R)-3-dodecyloxiran-2-yl)methanol；Oxiranemethanol, 3-dodecyl-, (2R,3R)-；[(2R,3R)-3-dodecyloxiran-2-yl]methanol
• CAS: 165880-19-3
• 化学式: C₁₅H₃₀O₂
• 分子量: 242.402
• InChiKey: FMRUDTZNVVEANW-HUUCEWRRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  17
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  32.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2R,3R)-2,3-Epoxypentadecan-1-ol 在 sodium chlorite 、 sodium dihydrogenphosphate 、 草酰氯 、 二甲基亚砜 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 (3S,4R)-3,4-epoxy-1-diazo-hexadecan-2-one
  参考文献：
  名称：

  通过顺序使用环氧重氮甲基酮的光诱导重排，合成（4R，5R）-多卡他霉素及其（4R，5S）-类似物

  摘要：

  合成了天然存在的δ-羟基-γ-内酯（4R，5R）-多卡他霉素及其非天然（4R，5S）-类似物。起始的非手性烯丙基醇被转化为α，β-环氧重氮甲基酮，随后这些化合物的立体定向辐射反应得到4-羟基-2-烯烃酯。以顺序的方式使用该方法，实现了立体异构中心的连续引入，产生了对映体纯的4，5-二羟基-2-烯烃酯。这些醇被转化为δ-羟基-γ-内酯Muricatacin。

  DOI：

  10.1016/0040-4020(95)00670-4
• 作为产物：
  描述：

  (E)-pentadec-2-en-1-ol 在 titanium(IV) isopropylate 、 叔丁基过氧化氢 、 (-)-diethyl tartrate 作用下， 以 二氯甲烷 为溶剂， 以78%的产率得到(2R,3R)-2,3-Epoxypentadecan-1-ol
  参考文献：
  名称：

  The first total synthesis of the 6-hydroxy-4E-sphingenines

  摘要：

  Ceramides containing the 6-hydroxy-4E-sphingenines, previously unknown long-chain bases, have recently been found in human skin. A total synthesis of 6-hydroxy-4E-sphingenines has been achieved. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)00390-3

文献信息

• C-1 Reactivity of 2,3-Epoxy Alcohols via Oxirane Opening with Metal Halides: Applications and Synthesis of Naturally Occurring 2,3-Octanediol, Muricatacin, 3-Octanol, and 4-Dodecanolide
  作者：Carlo Bonini、Chiara Federici、Leucio Rossi、Giuliana Righi

  DOI：10.1021/jo00120a025

  日期：1995.7

  The C-1 reactivity of 2,3-epoxy alcohols and derivatives has been examined thoroughly. In the first approach a rearrangement opening of 2,3-epoxy alcohols with LiI leads to 1-iodo 2,3-diols with erythro or three stereochemistry starting from trans or cis epoxy alcohols. Subsequent coupling with a carbon nucleophile can lead to a series of vicinal diols with predicted relative and absolute stereochemistry: the described methodology has been applied to the asymmetric synthesis of the naturally occurring (S,S)-2,3-octanediol and (R,R)-muricatacin. The second approach, starting from easily available tosyloxy epoxides, leads to the highly regioselective opening of the oxirane ring with Li halides. The 3-iodohydrins obtained can be reduced to the corresponding 1-(tosyloxy)alkan-2-ols and then coupled with common carbon nucleophiles to afford, in high yields, optically active alcohols. This methodology has been applied to the asymmetric synthesis of naturally occurring pheromones like 3(R)-octanol and 4(R)-dodecanolide.
• Synthesis of 6-Hydroxysphingosine and α-Hydroxy Ceramide Using a Cross-Metathesis Strategy
  作者：Patrick Wisse、Mark A. R. de Geus、Gen Cross、Adrianus M. C. H. van den Nieuwendijk、Eva J. van Rooden、Richard J. B. H. N. van den Berg、Johannes M. F. G. Aerts、Gijsbert A. van der Marel、Jeroen D. C. Codée、Herman S. Overkleeft

  DOI：10.1021/acs.joc.5b00823

  日期：2015.7.17

  In this paper, a new synthetic route toward 6-hydroxysphingosine and alpha-hydroxy ceramide is described. The synthesis employs a cross-metathesis to unite a sphingosine head allylic alcohol with a long-chain fatty acid alkene that also bears an allylic alcohol group. To allow for a productive CM coupling, the sphingosine head allylic alcohol was protected with a cyclic carbonate moiety and a reactive CM catalyst system, consisting of Grubbs II catalyst and CuI, was employed.
• Electrophilic selenocyclization in 2-ene-1,5-diol systems: unexpected oxetane vs. tetrahydrofuran formation
  作者：Pierre Van de Weghe、Stéphane Bourg、Jacques Eustache

  DOI：10.1016/s0040-4020(03)01134-7

  日期：2003.9

  Electrophile-induced cyclization of (E)- and (Z)-2-ene-1,5-diols to tetrahydrofurans and oxetanes is described. Significant differences between the present report and previous work have been noted. A tentative model is proposed. (C) 2003 Elsevier Ltd. All rights reserved.
• The first total synthesis of the 6-hydroxy-4E-sphingenines
  作者：J.S Yadav、V Geetha、A Krishnam Raju、D Gnaneshwar、S Chandrasekhar

  DOI：10.1016/s0040-4039(03)00390-3

  日期：2003.3

  Ceramides containing the 6-hydroxy-4E-sphingenines, previously unknown long-chain bases, have recently been found in human skin. A total synthesis of 6-hydroxy-4E-sphingenines has been achieved. (C) 2003 Elsevier Science Ltd. All rights reserved.
• Synthesis of (4R,5R)-muricatacin and its (4R,5S)-analog by sequential use of the photo-induced rearrangement of epoxy diazomethyl ketones
  作者：Marcel P.M. van Aar、Lambertus Thijs、Binne Zwanenburg

  DOI：10.1016/0040-4020(95)00670-4

  日期：1995.10

  The naturally occurring δ-hydroxy-γ-lactone (4R,5R)-muricatacin and its nonnatural (4R,5S)-analog are synthesized. The starting achiral allylic alcohols are converted into α,β-epoxy diazomethyl ketones followed by a stereospecific irradiation reaction of these compounds to give 4-hydroxy-2-alkene esters. Using this method in a sequential manner a successive introduction of stereogenic centers is realized

  合成了天然存在的δ-羟基-γ-内酯（4R，5R）-多卡他霉素及其非天然（4R，5S）-类似物。起始的非手性烯丙基醇被转化为α，β-环氧重氮甲基酮，随后这些化合物的立体定向辐射反应得到4-羟基-2-烯烃酯。以顺序的方式使用该方法，实现了立体异构中心的连续引入，产生了对映体纯的4，5-二羟基-2-烯烃酯。这些醇被转化为δ-羟基-γ-内酯Muricatacin。