(S)-1-((4S,5S)-5-((benzyloxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)but-3-yn-1-ol | 143360-25-2

• 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: (S)-1-((4S,5S)-5-((benzyloxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)but-3-yn-1-ol
• 英文别名: 1-(5-benzyloxymethyl-2,2-dimethyl[1,3]dioxolan-4-yl)but-3-yn-1-ol；(1S)-1-[(4S,5S)-2,2-dimethyl-5-(phenylmethoxymethyl)-1,3-dioxolan-4-yl]but-3-yn-1-ol
• CAS: 143360-25-2
• 化学式: C₁₇H₂₂O₄
• 分子量: 290.359
• InChiKey: DGRPDRANYZELCK-JYJNAYRXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-1-((4S,5S)-5-((benzyloxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)but-3-yn-1-ol 在 盐酸 、 甲醇 、 sodium periodate 、 silica gel 作用下， 以 甲苯 为溶剂， 反应 16.0h， 生成 6,8-dioxo-3,5,5a,6,7,8,8a,8b-octahydro-2H-1-oxa-7-aza-as-indacene-2-carbaldehyde
  参考文献：
  名称：

  Facile synthesis of enantiopure tricyclic furanyl derivatives via tungsten-mediated cycloalkenation reactions and Diels–Alder reactions

  摘要：

  Chiral furanyl diene 1 is easily prepared from cycloalkenation of chiral tungsten alkynol with acetaldehyde, followed by demetalation with Me3NO. This diene bears a chiral 1,3-dioxolane group to control diastereoselective Diels-Alder reactions with electron-deficient olefins. The chiral 1,3-dioxolane substituent of the cycloadducts was degraded to a hydrogen atom to make these molecules possess a common furanyl functionality. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)01815-4
• 作为产物：
  描述：

  (4S,5S)-4-benzyloxymethyl-5-hydroxymethyl-2,2-dimethyl-1,3-dioxolane 在 草酰氯 、 二甲基亚砜 、 锌 作用下， 以 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 13.0h， 生成 (S)-1-((4S,5S)-5-((benzyloxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)but-3-yn-1-ol
  参考文献：
  名称：

  A Facile Synthesis of Enantiopure Tricyclic Furanyl and Pyranyl Derivatives via Tungsten-Mediated Cycloalkenation and Diels−Alder Reaction

  摘要：

  We report the synthesis of chiral furanyl and pyranyl dienes 1 and 2 based on cycloalkenation of chiral tungsten alkynol complexes. These two dienes bear a chiral 1,3-dioxolane group to control diastereoselective Diels-Alder reactions with electron-deficient olefins. The chiral 1,3-dioxolane substituents of the cycloadducts were degraded into hydrogen atoms to make these molecules possess common furan and pyran rings. Dienes 1 and 2 are good building blocks for enantiopure forms of tricyclic oxygen compounds.

  DOI：

  10.1021/jo0205208

文献信息

• Convergent and stereoselective synthesis of (−)-zeaenol
  作者：Rayala Naveen Kumar、H.M. Meshram

  DOI：10.1016/j.tet.2015.06.035

  日期：2015.8

  Stereoselective synthesis of (−)-zeaenol has been accomplished from d-xylose as a chiral pool starting material. The key steps of this convergent synthetic strategy involves a Stille coupling, a Noyori reduction, a Julia–Kocienski olefination and a macrolactonization to obtain (−)-zeaenol. We have also explored a Sonogashira coupling along with a Trost protocol for the intramolecular hydrosilylation

  （-）-玉米醇的立体选择性合成已经由作为手性库起始材料的d-木糖完成。该聚合合成策略的关键步骤包括Stille偶联，Noyori还原，Julia-Kocienski烯烃化反应和大环内酯化反应以获得（-）-玉米醇。我们还探索了Sonogashira偶联以及Trost方案，用于在均丙醇体系上进行分子内氢化硅烷化，作为该分子的另一种合成方法。
• Synthesis of chiral oxacyclic dienes via ruthenium-catalyzed enyne metathesis: useful building blocks for chiral tricyclic oxygen derivatives
  作者：Hongyun Guo、Reniguntala J Madhushaw、Fwu-Ming Shen、Rai-Shung Liu

  DOI：10.1016/s0040-4020(02)00548-3

  日期：2002.7

  epimerization occurs at the oxacyclic carbon rather than the benzyl carbon. Diels–Alder reactions of chiral oxacyclic dienes 19 and 22 with maleic anhydride, maleimide and benzoquinone proceeded with high diastereoselectivities, yielding a single cycloadduct efficiently at ambient conditions. The structures of Diels–Alder adducts were determined by 1H NOE NMR spectra. The cycloadducts were formed via the

  各种手性氧杂环二烯均经由使用Grubbs催化剂（PCY烯炔复分解合成3）2氯2 RuCHPh。由（2S）-（苄氧基）-丙醛制备了一系列带有1,2-二醇骨架的底物。乙炔在23°C的CH 2 Cl 2中顺利进行，同时在乙烯气（1-2.5 atm）下以少量催化剂（2.0 mol％）负载，获得了高收率的产品，且在任何立体异构碳上均未发生差向异构化。加热料5在氮气下，在苯（80℃）中包含双取代炔烃的化合物导致通过初级产物的差向异构化而形成两个非对映异构体。差向异构化发生在氧杂环碳而不是苄基碳。手性乙二环二烯19和22与顺丁烯二酸酐，顺丁烯二酰亚胺和苯醌的狄尔斯-阿尔德反应具有很高的非对映选择性，在环境条件下可以有效地生成单个环加合物。Diels–Alder加合物的结构由1 H NOE NMR光谱确定。环加合物经由亲二烯体以内模方式与立体异构中心的取代基相反的二烯形成。环加合物29和31将（2S）-
• Diastereoselective Propargylation of .alpha.-Alkoxy Aldehydes with Propargyl Bromide and Zinc. A Versatile and Efficient Method for the Synthesis of Chiral Oxygenated Acyclic Natural Products
  作者：Wen-Lian Wu、Zhu-Jun Yao、Yun-Long Li、Jin-Cui Li、Yi Xia、Yu-Lin Wu

  DOI：10.1021/jo00115a049

  日期：1995.5
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  作者：Wu Wen-Lian、wu Yu-Lin

  DOI：10.1016/s0040-4039(00)74811-8

  日期：1992.6