Acetic acid (2R,3S,6S)-2-acetoxymethyl-6-(4-tert-butyl-phenylethynyl)-3,6-dihydro-2H-pyran-3-yl ester | 915772-00-8

• 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: Acetic acid (2R,3S,6S)-2-acetoxymethyl-6-(4-tert-butyl-phenylethynyl)-3,6-dihydro-2H-pyran-3-yl ester
• 英文别名: [(2R,3S,6S)-3-acetyloxy-6-[2-(4-tert-butylphenyl)ethynyl]-3,6-dihydro-2H-pyran-2-yl]methyl acetate
• CAS: 915772-00-8
• 化学式: C₂₂H₂₆O₅
• 分子量: 370.445
• InChiKey: OLDTWKJGJZXYRD-QHAWAJNXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Acetic acid (2R,3S,6S)-2-acetoxymethyl-6-(4-tert-butyl-phenylethynyl)-3,6-dihydro-2H-pyran-3-yl ester 在 吡啶 、 macroporous carbonate resin 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 18.0h， 生成 Carbonic acid (2R,3S,6S)-6-(4-tert-butyl-phenylethynyl)-2-ethoxycarbonyloxymethyl-3,6-dihydro-2H-pyran-3-yl ester ethyl ester
  参考文献：
  名称：

  通过糖基支架的环收缩探索骨骼多样性。

  摘要：

  芳基醚C-糖苷支架已由C-糖基化，然后由Pd（0）介导的苯酚进行烯丙基取代，由三-O-乙酰基-D-葡糖醛制备。使芳基醚经历[3,3]-σ重排以产生3-吡喃基-酚或Au（III）介导的环收缩以产生高度取代的四氢呋喃。[结构：见文字]

  DOI：

  10.1021/ol0618252
• 作为产物：
  描述：

  4-叔-丁基苯基乙炔 在 zinc(II) chloride 、 scandium tris(trifluoromethanesulfonate) 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 5.25h， 生成 Acetic acid (2R,3S,6S)-2-acetoxymethyl-6-(4-tert-butyl-phenylethynyl)-3,6-dihydro-2H-pyran-3-yl ester
  参考文献：
  名称：

  通过糖基支架的环收缩探索骨骼多样性。

  摘要：

  芳基醚C-糖苷支架已由C-糖基化，然后由Pd（0）介导的苯酚进行烯丙基取代，由三-O-乙酰基-D-葡糖醛制备。使芳基醚经历[3,3]-σ重排以产生3-吡喃基-酚或Au（III）介导的环收缩以产生高度取代的四氢呋喃。[结构：见文字]

  DOI：

  10.1021/ol0618252

文献信息

• Gold-Catalyzed Vinyl Ether Hydroalkynylation: An Alternative Pathway for the Gold-Catalyzed Intermolecular Reaction of Alkenes and Alkynes
  作者：Seyedmorteza Hosseyni、Courtney A. Smith、Xiaodong Shi

  DOI：10.1021/acs.orglett.6b03228

  日期：2016.12.16

  this report, the gold-catalyzed intermolecular reaction of vinyl ethers and terminal alkynes is investigated. Utilizing a triazole gold catalyst lessens gold decomposition in the presence of the vinyl ether and affords an alkynylation product instead of the [2 + 2] product. This protocol has been expanded to include glycal substrates, which undergo a one-pot alkynylation–Ferrier reaction to produce functionalized

  在本报告中，研究了金催化的乙烯基醚和末端炔烃的分子间反应。使用三唑金催化剂减少了乙烯基醚存在下金的分解，并提供了炔基化产物而不是[2 + 2]产物。该方案已扩展到包括糖基底物，该底物经过一锅炔基化-费里尔反应，以中等至优异的产率和高非对映选择性生产功能化糖。
• Zinc mediated activation of terminal alkynes: stereoselective synthesis of alkynyl glycosides
  作者：Madhu Babu Tatina、Anil Kumar Kusunuru、Syed Khalid Yousuf、Debaraj Mukherjee

  DOI：10.1039/c4ob01405g

  日期：——

  mediated alkynylation reaction was studied for the preparation of C-glycosides from unactivated alkynes. Different glycosyl donors such as glycals and anomeric acetates were tested towards an alkynyl zinc reagent obtained from alkynes using zinc dust and ethyl bromoacetate as an additive. The method provides simple, mild and stereoselective access to alkynyl glycosides both from aromatic and aliphatic acetylenes

  研究了锌介导的炔基化反应，用于从未活化的炔烃制备C-糖苷。使用锌粉和溴乙酸乙酯作为添加剂，对从炔烃制得的炔基锌试剂进行了测试，测试了不同的糖基供体（例如，乙二醇和异头乙酸酯）。该方法提供了从芳族和脂族乙炔对炔基糖苷的简单，温和和立体选择。
• A general metal-free approach for the stereoselective synthesis of <i>C</i>-glycals from unactivated alkynes
  作者：Shekaraiah Devari、Manjeet Kumar、Ramesh Deshidi、Masood Rizvi、Bhahwal Ali Shah

  DOI：10.3762/bjoc.10.277

  日期：——

  A novel metal-free strategy for a rapid and α-selctive C-alkynylation of glycals was developed. The reaction utilizes TMSOTf as a promoter to generate in situ trimethylsilylacetylene for C-alkynylation. Thanks to this methodology, we can access C-glycosides in a single step from a variety of acetylenes , i.e., arylacetylenes and most importantly aliphatic alkynes.

  开发了一种新颖的无金属策略，用于快速和α-选择性的甘露醇基的C-炔基化。该反应利用TMSOTf作为促进剂，生成原位三甲基硅乙炔用于C-炔基化。借助这种方法，我们可以从各种乙炔（如芳基乙炔和最重要的脂肪族炔烃）中以单步方式获得C-糖苷。
• Skeletal Diversity via Cationic Rearrangements of Substituted Dihydropyrans
  作者：Matthew R. Medeiros、Radha S. Narayan、Nolan T. McDougal、Scott E. Schaus、John A. Porco

  DOI：10.1021/ol101144k

  日期：2010.7.16

  Substituted dihydropyrans, easily accessed from a commercially available glycal, undergo acid-catalyzed rearrangement to provide highly functionalized isochroman and dioxabicyclooctane scaffolds.

  取代的二氢吡喃很容易从市售的糖基中获得，经过酸催化重排以提供高度官能化的异色满和二氧杂双环辛烷支架。
• Exploring Skeletal Diversity via Ring Contraction of Glycal-Derived Scaffolds
  作者：Adam R. Yeager、Geanna K. Min、John A. Porco,、Scott E. Schaus

  DOI：10.1021/ol0618252

  日期：2006.10.1

  Aryl ether C-glycoside scaffolds have been prepared from tri-O-acetyl-D-glucal by C-glycosylation followed by allylic substitution with phenols mediated by Pd(0). The aryl ethers were subjected to either [3,3]-sigmatropic rearrangement to produce 3-pyranyl-phenols or Au(III)-mediated ring contraction to create highly substituted tetrahydrofurans. [structure: see text]

  芳基醚C-糖苷支架已由C-糖基化，然后由Pd（0）介导的苯酚进行烯丙基取代，由三-O-乙酰基-D-葡糖醛制备。使芳基醚经历[3,3]-σ重排以产生3-吡喃基-酚或Au（III）介导的环收缩以产生高度取代的四氢呋喃。[结构：见文字]