1-(4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl)-2-(p-tolyl)ethyne | 1082737-48-1

• 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: 1-(4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl)-2-(p-tolyl)ethyne
• 英文别名: [(2R,3S,6S)-3-acetyloxy-6-[2-(4-methylphenyl)ethynyl]-3,6-dihydro-2H-pyran-2-yl]methyl acetate
• CAS: 1082737-48-1
• 化学式: C₁₉H₂₀O₅
• 分子量: 328.365
• InChiKey: UNVMVWQWBMUMFX-CEXWTWQISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.37
• 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：

  乙酰化葡萄烯糖 、 4-甲苯基乙炔 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 0.03h， 以84%的产率得到1-(4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl)-2-(p-tolyl)ethyne
  参考文献：
  名称：

  A general metal-free approach for the stereoselective synthesis of C-glycals from unactivated alkynes

  摘要：

  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。

  DOI：

  10.3762/bjoc.10.277

文献信息

• 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。
• 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。
• Copper mediated stereoselective synthesis of C-glycosides from unactivated alkynes
  作者：Anil Kumar Kusunuru、Madhubabu Tatina、Syed Khalid Yousuf、Debaraj Mukherjee

  DOI：10.1039/c3cc44250k

  日期：——

  A highly stereoselective rapid C-glycosylation reaction has been developed between glycal and unactivated alkynes in the presence of coppertriflate and ascorbic acid at low catalyst loading and at room temperature. A wide variety of glycals and aryl acetylenes participate in the reaction smoothly. TfOH generated during the reduction of Cu(OTf)2 by ascorbic acid may be the active catalyst for the glycosylation.

  在低催化剂载量和室温条件下，在三氟氯酸铜和抗坏血酸存在下，开发出了一种高度立体选择性的甘氨醛和未活化炔烃之间的快速 C-糖基化反应。多种甘氨醛和芳基炔烃顺利地参与了反应。抗坏血酸还原 Cu(OTf)2 时生成的 TfOH 可能是糖基化反应的活性催化剂。
• 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.