1-(4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl)-2-cyclopropylethyne | 1082737-50-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 奥昔康唑
• 英文名称: 1-(4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl)-2-cyclopropylethyne
• 英文别名: [(2R,3S,6S)-3-acetyloxy-6-(2-cyclopropylethynyl)-3,6-dihydro-2H-pyran-2-yl]methyl acetate
• CAS: 1082737-50-5
• 化学式: C₁₅H₁₈O₅
• 分子量: 278.305
• InChiKey: FHECIUMOKPVTNJ-QLFBSQMISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  环丙乙炔 、 乙酰化葡萄烯糖 在 溴乙酸乙酯 、 锌 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以72%的产率得到1-(4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl)-2-cyclopropylethyne
  参考文献：
  名称：

  锌介导的末端炔烃活化：炔基糖苷的立体选择性合成† •

  摘要：

  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。

  DOI：

  10.1039/c4ob01405g

文献信息

• Transformation of Glycals into α,β,γ,δ-Conjugated Chirons under Metal-Free Conditions
  作者：Tatina Madhubabu、Syed Khalid Yousuf、Anil Kumar Kusunuru、Debaraj Mukherjee

  DOI：10.1002/ejoc.201403041

  日期：2014.11

  A diastereoselective, metal-free, one-pot domino synthetic strategy was developed for the transformation of glycals into new chiral scaffolds. Optimization of the reaction conditions to exclude normal Ferrier products, characterization of the new entities, and a plausible mechanism were investigated.

  开发了一种非对映选择性、无金属、一锅多米诺骨牌合成策略，用于将糖类转化为新的手性支架。研究了排除正常 Ferrier 产物的反应条件优化、新实体的表征和可能的机制。
• 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。
• Nucleophilic Addition of Potassium Alkynyltrifluoroborates to <scp>d</scp>-Glucal Mediated by BF₃·OEt₂: Highly Stereoselective Synthesis of α-<i>C</i>-glycosides
  作者：Adriano S. Vieira、Pedro F. Fiorante、Thomas L. S. Hough、Fernando P. Ferreira、Diogo S. Lüdtke、Hélio A. Stefani

  DOI：10.1021/ol8022177

  日期：2008.11.20

  A convenient, mild and highly stereoselective method for C-glycosidation (alkynylation) of D-glucal with various potassium alkynyltrifluoroborates, mediated by BF3 center dot OEt2 and involving oxonium intermediates, preferentially provides the alpha-acetylene glycoside products with good yields.