1α-ethynyl-1,2-dideoxy-3,5-di-O-(4-toluoyl)-D-ribofuranose | 396131-30-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1α-ethynyl-1,2-dideoxy-3,5-di-O-(4-toluoyl)-D-ribofuranose
• 英文别名: [(2R,3S,5S)-5-ethynyl-3-(4-methylbenzoyl)oxyoxolan-2-yl]methyl 4-methylbenzoate
• CAS: 396131-30-9
• 化学式: C₂₃H₂₂O₅
• 分子量: 378.425
• InChiKey: HKQUMHRKYCBRDD-QHAWAJNXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 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：

  1α-ethynyl-1,2-dideoxy-3,5-di-O-(4-toluoyl)-D-ribofuranose 在 四(三苯基膦)钯 、 (Z)-3-碘丙烯酸 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 48.0h， 以60%的产率得到1,4-bis[1,2-dideoxy-3,5-di-O-(4-toluoyl)-α-D-ribofuranosyl]butadiyne
  参考文献：
  名称：

  生物活性γ-亚烷基丁烯内酯库的扩展

  摘要：

  -具有脱氧核苷、类固醇和茂金属部分的亚烷基丁烯内酯是通过立体选择性顺序交叉偶联内酯化过程从相应的官能化末端炔烃与 3-碘丙烯酸合成的。丁烯内酯环形成的高选择性由 Pd/Cu 盐比保证。测试所得化合物的抗真菌和细胞抑制特性。最值得注意的是，带有脱氧核苷部分的γ-亚烷基丁烯内酯在微摩尔范围内显示出有希望的细胞抑制活性。

  DOI：

  10.1055/s-0028-1083181
• 作为产物：
  描述：

  1-Α-氯-3,5-二-O-对甲苯甲酰基-2-脱氧-D-呋喃核糖 、 乙炔基溴化镁 在 iron(III) chloride 、 四甲基乙二胺 作用下， 反应 3.0h， 生成 1β-ethynyl-1,2-dideoxy-3,5-di-O-(4-toluoyl)-D-ribofuranose 、 1α-ethynyl-1,2-dideoxy-3,5-di-O-(4-toluoyl)-D-ribofuranose
  参考文献：
  名称：

  Sonogashira reactions of α- and β-1-ethynyl-2-deoxyribosides: synthesis of acetylene-extended C-nucleosides

  摘要：

  An improved practical protocol for the synthesis of both anomers of 1-ethynyl-2-deoxiribosides 1 was developed. The Sonogashira coupling of ethynyldeoxyribosides 1 with various aryl- and heteroaryl halides was carried out under various conditions. It was found that the use of copper-free coupling protocols could reduce the oxidative dimerisation in favour of arylalkynyldeoxyriboside formation. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.11.030

文献信息

• Extension of the Library of Biologically Active γ-Alkylidene Butenolides
  作者：Martin Kotora、Petr Novák、Milan Pour、Marcel Špulák、Ivan Votruba

  DOI：10.1055/s-0028-1083181

  日期：——

  -Alkylidene butenolides bearing a deoxyriboside, a steroid, and a metallocene moiety were synthesized by stereoselective sequential cross-coupling lactonization procedure from the corresponding functionalized terminal alkynes with 3-iodopropenoic acids. The high selectivity of the butenolide ring formation was secured by the Pd/Cu salt ratio. The resulting compounds were tested for antifungal and cytostatic

  -具有脱氧核苷、类固醇和茂金属部分的亚烷基丁烯内酯是通过立体选择性顺序交叉偶联内酯化过程从相应的官能化末端炔烃与 3-碘丙烯酸合成的。丁烯内酯环形成的高选择性由 Pd/Cu 盐比保证。测试所得化合物的抗真菌和细胞抑制特性。最值得注意的是，带有脱氧核苷部分的γ-亚烷基丁烯内酯在微摩尔范围内显示出有希望的细胞抑制活性。
• Modular synthesis of 1-α- and 1-β-(indol-2-yl)-2′-deoxyribose C-nucleosides
  作者：David Nečas、Denisa Hidasová、Michal Hocek、Martin Kotora

  DOI：10.1039/c1ob05844d

  日期：——

  A simple two-step method for the selective preparation of anomerically pure 1α- and 1β-(indol-2-yl)deoxyribose derivatives was developed. The synthesis was based on the Sonogashira reaction of 1α- and 1β-ethynyldeoxyribose and 2-haloanilines followed by a Pd-complex catalyzed cyclization to the corresponding indolyldeoxyribosides.

  本研究开发了一种简单的两步法，用于选择性地制备同分异构体纯的 1δ-和 1δ-(吲哚-2-基)脱氧核糖衍生物。该合成基于 1δ-和 1δ-²-乙炔基脱氧核糖与 2-卤代苯胺的 Sonogashira 反应，然后在钯络合物催化下环化成相应的吲哚基脱氧核苷。
• Synthesis of C-Aryldeoxyribosides by [2 + 2 + 2]-Cyclotrimerization Catalyzed by Rh, Ni, Co, and Ru Complexes
  作者：Petr Novák、Radek Pohl、Martin Kotora、Michal Hocek

  DOI：10.1021/ol060454m

  日期：2006.5.1

  developed. Cyclotrimerization of C-alkynyldeoxyriboside with a variety of substituted 1,6-heptadiynes to the corresponding C-aryldeoxyribosides was catalyzed by various transition metal complexes (Rh, Ir, Co, Ru, and Ni). The most general catalyst proved to be RhCl(PPh(3))(3), which could catalyze most of the cyclotrimerizations in high yields (52-95%).

  [反应：见正文]开发了一种合成功能化C-核苷的新方法。通过各种过渡金属络合物（Rh，Ir，Co，Ru和Ni）催化具有各种取代的1,6-庚二炔的C-炔基脱氧核糖苷环化为相应的C-芳基脱氧核糖苷。事实证明，最通用的催化剂是RhCl（PPh（3））（3），可以高产率（52-95％）催化大多数环三聚反应。
• Co- and homocyclotrimerization reactions of protected 1-alkynyl-2-deoxyribofuranose. Synthesis of C-nucleosides, C-di- and C-trisaccharide analogues
  作者：Petr Novák、Sylva Číhalová、Miroslav Otmar、Michal Hocek、Martin Kotora

  DOI：10.1016/j.tet.2008.03.046

  日期：2008.5

  Cyclotrimerization of beta- or alpha-ethynyl-3,5-di-O-toluoyl-2-deoxy-D-ribofuranose with alpha,omega-diynes proceeded smoothly under Rh-catalysis to afford the corresponding beta- or a-benzene C-nucleoside derivatives. Analogous co-cyclotrimerization of alpha- or beta-propynyl- and -phenylethynyl-3,5-di-O-toluoyl-2-deoxy-D-ribofuranose with alpha,omega-diynes gave the corresponding arene derivatives only under microwave irradiation in the presence of a Rh-catalyst in moderate yields. Attempted homocyclotrimerization of beta- or alpha-ethynyl-3,5-di-O-toluoyl-2-deoxy-D-ribofuranose under Rh-catalysis led only to enynes while the use of Ru-catalyst gave the desired 1,2,4- and 1,3,5-tri-(2-deoxyribofuranose-1-yl)benzene. (c) 2008 Elsevier Ltd. All rights reserved.
• Sonogashira reactions of α- and β-1-ethynyl-2-deoxyribosides: synthesis of acetylene-extended C-nucleosides
  作者：Tomáš Bobula、Michal Hocek、Martin Kotora

  DOI：10.1016/j.tet.2009.11.030

  日期：2010.1

  An improved practical protocol for the synthesis of both anomers of 1-ethynyl-2-deoxiribosides 1 was developed. The Sonogashira coupling of ethynyldeoxyribosides 1 with various aryl- and heteroaryl halides was carried out under various conditions. It was found that the use of copper-free coupling protocols could reduce the oxidative dimerisation in favour of arylalkynyldeoxyriboside formation. (C) 2009 Elsevier Ltd. All rights reserved.