[(2R,3R,4R,5R)-3,4-diacetyloxy-5-(5-iodo-4-phenyltriazol-1-yl)oxolan-2-yl]methyl acetate | 1021183-22-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(2R,3R,4R,5R)-3,4-diacetyloxy-5-(5-iodo-4-phenyltriazol-1-yl)oxolan-2-yl]methyl acetate
• CAS: 1021183-22-1
• 化学式: C₁₉H₂₀IN₃O₇
• 分子量: 529.288
• InChiKey: UKZLLCRATRMIQD-KLICCBINSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  30
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  119
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  1-azido-2,3,4-tri-O-acetylribose 、 苯乙炔 在 copper(l) iodide 、 四乙基碘化铵 、 Selectfluor 、 N,N-二异丙基乙胺 作用下， 以 水 为溶剂， 反应 5.0h， 以69%的产率得到[(2R,3R,4R,5R)-3,4-diacetyloxy-5-(5-iodo-4-phenyltriazol-1-yl)oxolan-2-yl]methyl acetate
  参考文献：
  名称：

  在空气中使用含水碘化系统新型合成5-碘-1,2,3-三唑

  摘要：

  开发了一种新颖的碘化水溶液体系，用于在空气中合成5-碘-1,2,3-三唑。该反应体系具有高效率和优异的化学选择性，且具有宽泛的官能团耐受性。此外，该方法可用于修饰生物分子（如核糖和核苷），并在与其他反应类型（如Sonogashira反应）结合时用于生物分子的双标记。

  DOI：

  10.1016/j.tetlet.2018.08.039

文献信息

• A Convenient Preparation of 5-Iodo-1,4-disubstituted-1,2,3-triazole: Multicomponent One-Pot Reaction of Azide and Alkyne Mediated by CuI−NBS
  作者：Lingjun Li、Guisheng Zhang、Anlian Zhu、Lihe Zhang

  DOI：10.1021/jo800035v

  日期：2008.5.1

  The system of CuI and NBS was found to provide both I+ and Cu+ for the first time. An efficient method for preparation of 5-iodo-1,4-disubstituted-1,2,3-triazole was achieved by multicomponent one-pot reaction of azides with alkynes in the presence of the novel CuI and NBS catalytic system. The high tolerance of various sensitive groups revealed the potential applications of this method in organic

  发现CuI和NBS系统首次提供I +和Cu +。在新型CuI和NBS催化体系的存在下，通过叠氮化物与炔烃的多组分一锅反应，实现了制备5-碘-1,4-二取代-1,2,3-三唑的有效方法。各种敏感性基团的高耐受性揭示了该方法在有机合成和药物发现中的潜在应用。
• A New Synthetic Protocol for One-Pot Preparations of 5-Halo-1,4-disubstituted-1,2,3-triazoles
  作者：Lingjun Li、Yanyan Li、Ran Li、Anlian Zhu、Guisheng Zhang

  DOI：10.1071/ch11067

  日期：——

  In this paper, a new synthetic protocol for one-pot preparations of 5-halo-1,4-disubstituted-1,2,3-triazoles is provided by rational combination of a CuI catalyzed azide–alkyne cycloaddition (CuAAC) reaction and an oxidative halogenation reaction. CuI- N-chlorosuccinimide (NCS) and CuBr-NCS reaction systems are developed, respectively, for effective preparations of 5-iodo-1,4-disubstituted-1,2,3-triazoles and 5-bromo-1,4-disubstituted-1,2,3-trizoles under mild conditions with a high tolerance of various sensitive groups.

  本文通过合理结合 CuI 催化的叠氮-炔环加成反应（CuAAC）和氧化卤化反应，提供了一种一锅制备 5-卤代-1,4-二取代-1,2,3-三唑的新合成方案。CuI- N-氯代丁二酰亚胺（NCS）和 CuBr-NCS 反应体系分别用于在温和条件下有效制备 5-碘-1,4-二取代-1,2,3-三唑和 5-溴-1,4-二取代-1,2,3-三唑，对各种敏感基团具有很高的耐受性。
• Multicomponent Aqueous Synthesis of Iodo-1,2,3-triazoles: Single-Step Models for Dual Modification of Free Peptide and Radioactive Iodo Labeling
  作者：Lingjun Li、Shengqiang Ding、Yanping Yang、Anlian Zhu、Xincui Fan、Mengchao Cui、Changpo Chen、Guisheng Zhang

  DOI：10.1002/chem.201605034

  日期：2017.1.23

  direct modification of bioactive molecules in water. Through the combination of water‐compatible oxidative iodination and the copper‐catalyzed alkyne–azide cycloaddition reaction, a novel copper‐catalyzed aqueous multicomponent synthetic method for the preparation of 5‐iodo‐1,2,3‐triazoles has been developed. The method is highly effective and selective for substrates including biologically relevant

  碘1,2,3-三唑在化学和生物医学应用中具有相当大的兴趣。然而，目前制备碘1,2,3-三唑的合成方法不能轻易地应用于水中生物活性分子的直接修饰。通过水相容性氧化碘化和铜催化的炔-叠氮化物环加成反应的结合，开发了一种新颖的铜催化的水性多组分合成方法，用于制备5-碘，1,2,3-三唑。该方法对包括具有核苷，糖和氨基酸部分的生物相关化合物的底物是高效和选择性的。基于这种水性串联反应，从容易获得的起始原料开发了直接的单步多组分双修饰肽。此外，由可商购获得的125碘化钠水溶液作为起始原料进行125 I标记。
• Three-component assembly of 5-halo-1,2,3-triazoles via aerobic oxidative halogenation
  作者：Lingjun Li、Guoliang Hao、Anlian Zhu、Sangui Liu、Guisheng Zhang

  DOI：10.1016/j.tetlet.2013.08.089

  日期：2013.11

  An effective synthetic protocol for 5-halo-1,2,3-triazoles was developed by novel TBDMSCI (tert-butyldi-methylsily1 chloride)-activated aerobic oxidative halogenations in this Letter. TBDMSCI, for the first time, was found to activate aerobic oxidation of CuX to produce X-2 with Cu+ which then could effectively promote one-pot syntheses of 5-halo-1,2,3-triazole from alkyne, azide, and CuX (X = I, Br) under O-2 atmosphere at room temperature. The advantages in this method include inexpensive and green O-2 as oxidant, use of mild and non-oxidative additive, and wide scope of substrates. (C) 2013 Elsevier Ltd. All rights reserved.