1-(4,6-di-O-acetyl-2,3-dideoxy-D-erythro-hex-2-enopyranosyl)oct-1-yne | 906665-15-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: 1-(4,6-di-O-acetyl-2,3-dideoxy-D-erythro-hex-2-enopyranosyl)oct-1-yne
• 英文别名: 1-(4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl)-oct-1-yne；[(2R,3S,6S)-3-acetyloxy-6-oct-1-ynyl-3,6-dihydro-2H-pyran-2-yl]methyl acetate
• CAS: 906665-15-4
• 化学式: C₁₈H₂₆O₅
• 分子量: 322.401
• InChiKey: NIKAMBWYHURJTP-FGTMMUONSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  23
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 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：

  1-(4,6-di-O-acetyl-2,3-dideoxy-D-erythro-hex-2-enopyranosyl)oct-1-yne 在 吡啶 、 macroporous carbonate resin 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 30.0h， 生成 [(2R,3S,6S)-2-(ethoxycarbonyloxymethyl)-6-oct-1-ynyl-3,6-dihydro-2H-pyran-3-yl] ethyl carbonate
  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：

  1-辛炔 在 indium 吗啉 、 碘 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 18.0h， 生成 1-(4,6-di-O-acetyl-2,3-dideoxy-D-erythro-hex-2-enopyranosyl)oct-1-yne
  参考文献：
  名称：

  Ferrier-Type Alkynylation Reaction Mediated by Indium

  摘要：

  An efficient Ferrier-type alkynylation reaction between glycals and iodoalkynes using Barbier conditions is described. These conditions require In-0, In-I, or In-II and lead to alpha-2,3-unsaturated-C-glycosides with good stereoselectivity. When glycosyliodoalkynes are used, trehalose-derived compounds and alpha-(1 -> 6)-C-disaccharides are obtained.

  DOI：

  10.1021/ol701480x

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。
• 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。
• Highly stereoselective synthesis of C-(alkynyl)-pseudoglycals from δ-hydroxy-α,β-unsaturated aldehydes
  作者：J.S. Yadav、A. Krishnam Raju、V. Sunitha

  DOI：10.1016/j.tetlet.2006.05.159

  日期：2006.7

  An efficient and novel methodology for the synthesis of C-(alkynyl)-pseudoglycals from delta-hydroxy-alpha,beta-unsaturated aldehydes has been developed. (c) 2006 Elsevier Ltd. All rights reserved.
• 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.