3-O-benzyl-1,2-O-isopropylidene-5-O-propargyl-α-D-xylofuranose | 1005198-86-6

• 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: 3-O-benzyl-1,2-O-isopropylidene-5-O-propargyl-α-D-xylofuranose
• 英文别名: (3aR,5R,6S,6aR)-6-(benzyloxy)-2,2-dimethyl-5-((prop-2-ynyloxy)methyl)tetrahydrofuro[2,3-d][1,3]dioxole；(3aR,5R,6S,6aR)-2,2-dimethyl-6-phenylmethoxy-5-(prop-2-ynoxymethyl)-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxole
• CAS: 1005198-86-6
• 化学式: C₁₈H₂₂O₅
• 分子量: 318.37
• InChiKey: NMGCLLXMHLDWPH-YYIAUSFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  46.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-O-benzyl-1,2-O-isopropylidene-5-O-propargyl-α-D-xylofuranose 在 sodium azide 、 Cu*O₄S^(2-)*5H₂O 、 sodium hydride 、 sodium ascorbate 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.33h， 生成 6-(4-(3-O-benzyl-5-O-methylene-1,2-O-isopropylidene-α-D-xylofuranose)-1H-1,2,3-triazol-1-yl)-6,7-dihydro-4H-[1,2,3]triazolo[5,1-c][1,4]oxazine
  参考文献：
  名称：

  Click Chemistry Inspired Synthesis of Morpholine-Fused Triazoles

  摘要：

  The synthesis of triazolyl azido alcohols from terminal alkyne via oxirane ring-opening of epichlorohydrin, followed by click reaction with alkynes, and subsequent azidation of chlorohydroxy triazoles was achieved under a one-pot methodology. The developed triazolyl azido alcohols were further utilized for the synthesis of a diverse range of morpholine-fused triazoles of chemotherapeutic value. The structure of all developed compounds has been elucidated using IR. NMR, MS, and elemental analysis, where four of them have been characterized by single-crystal X-ray analysis.

  DOI：

  10.1021/jo500890w
• 作为产物：
  描述：

  3-O-benzyl-1,2-O-isopropylidene-α-D-xylofuranose 、 3-溴丙炔 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 生成 3-O-benzyl-1,2-O-isopropylidene-5-O-propargyl-α-D-xylofuranose
  参考文献：
  名称：

  新型异恶唑连接的甾体糖共轭物的合成-新型甾体一氧化氮的应用

  摘要：

  异恶唑连接的甾族糖共轭物是通过原位生成的，迄今未知的甾族腈氧化物与适当的糖炔丙基醚的1,3-偶极环加成反应制备的。该方法以易于获得的一氧化二氮的形式提供了一种新颖的载体，其具有与许多生物分子偶联的能力，从而提供了构建生物学上重要的新型甾体缀合物的新途径。

  DOI：

  10.1016/j.tetlet.2008.01.130

文献信息

• Allyloxy and Propargyloxy Group Migration: Role of Remote Group Participation in the Synthesis of 5-C-Nucleosides and Other Sugar Derivatives
  作者：Subhrangshu Mukherjee、Prabhash N. Tripathi、Sukhendu B. Mandal

  DOI：10.1021/ol301851q

  日期：2012.8.17

  In 1-deoxy-xylofuranose derivatives possessing a good leaving group at 2-C, participation of allyloxy and propargyloxy substituents at 5-C results in loss of the 2-C substituent and attack of various nucleophiles at 5-C of the oxonium intermediate. Such participation of a benzyloxy or crotyloxy group leads to dioxabicyclo[2.2.1]heptane rings.

  在2-C处具有良好离去基团的1-脱氧-木呋喃糖衍生物中，烯丙基氧基和炔丙基氧基取代基在5-C处的参与导致2-C取代基的丢失和各种亲核试剂在氧中间体的5-C处的进攻。苄氧基或巴豆氧基的这种参与导致二氧杂双环[2.2.1]庚烷环。
• Regioselective facile synthesis of novel isoxazole-linked glycoconjugates
  作者：Amrita Mishra、Bhuwan B. Mishra、Vinod K. Tiwari

  DOI：10.1039/c5ra05905d

  日期：——

  A concise and efficacious protocol for the regioselective synthesis of novel 3,5-disubstituted isoxazole-linked glycoconjugates (4, 7 and 9) via a 1,3-dipolar cycloaddition reaction between in situ generated glycosyl-β-nitrile oxide (derived from glycosyl-β-nitromethane ester 3 and 6) and various terminal alkynes bearing sugar, alkyl and aryl substituents (2a–n), has been devised. The formation of

  简明和有效的协议，用于新颖的3,5-二取代的异恶唑联糖缀合物（的区域选择性合成4,7和9）通过1,3-偶极环加成反应之间原位产生的糖基- β-氧化腈（来自糖基衍生-β-硝基甲烷酯3和6）以及带有糖，烷基和芳基取代基（2a–n）的各种末端炔烃已被设计出来。DFT计算支持了反应过程中一氧化氮的形成，从而给出了糖基-β-腈氧化物酯的优化结构。这种一锅法的方法提供了一种利用D的方法-葡萄糖衍生的一氧化氮，作为点击化学中新的变异体，用于合成新型异恶唑连接的糖缀合物，为构建基于碳水化合物的多方面生物学特征的支架开辟了一条新途径。
• Synthesis of isoxazole conjugates of sugars via 1,3-dipolar cycloaddition
  作者：Vipraja V Vaidya、Karuna S Wankhede、Manikrao M Salunkhe、Girish K Trivedi

  DOI：10.1139/v07-145

  日期：2008.2.1

  Isoxazole conjugates of sugar have been synthesized by the aid of 1,3-dipolar cycloaddition in a click chemistry approach. The sugar-derived propargyl ethers underwent 1,3-dipolar cycloadditions smoothly with in situ generated nitrile oxides from aromatic oximes in good yields. The reaction exhibited a high degree of regioselectivity.Key words: isoxazole conjugates, 1,3-dipolar cycloadditions, nitrile oxides.

  在点击化学方法中，借助 1,3-二极环加成法合成了糖的异噁唑共轭物。由糖衍生的丙炔醚与原位生成的芳香氧化物中的腈氧化物顺利进行了 1,3-二极环加成反应，产率良好。该反应具有高度的区域选择性。
• Synthesis of novel isoxazole-linked steroidal glycoconjugates—an application of a novel steroidal nitrile oxide
  作者：Karuna S. Wankhede、Vipraja V. Vaidya、Prajakta S. Sarang、Manikrao M. Salunkhe、Girish K. Trivedi

  DOI：10.1016/j.tetlet.2008.01.130

  日期：2008.3

  glycoconjugates are prepared by 1,3-dipolar cycloaddition reactions of an in situ generated and hitherto unknown steroidal nitrile oxide with appropriate propargyl ethers of sugars. The methodology provides a novel vector in the form of an easily accessible nitrile oxide having the ability to couple with many biomolecules, thus offering a new pathway to construct biologically significant novel steroidal conjugates

  异恶唑连接的甾族糖共轭物是通过原位生成的，迄今未知的甾族腈氧化物与适当的糖炔丙基醚的1,3-偶极环加成反应制备的。该方法以易于获得的一氧化二氮的形式提供了一种新颖的载体，其具有与许多生物分子偶联的能力，从而提供了构建生物学上重要的新型甾体缀合物的新途径。
• Click Chemistry Inspired Synthesis of Morpholine-Fused Triazoles
  作者：Kunj B. Mishra、Vinod K. Tiwari

  DOI：10.1021/jo500890w

  日期：2014.6.20

  The synthesis of triazolyl azido alcohols from terminal alkyne via oxirane ring-opening of epichlorohydrin, followed by click reaction with alkynes, and subsequent azidation of chlorohydroxy triazoles was achieved under a one-pot methodology. The developed triazolyl azido alcohols were further utilized for the synthesis of a diverse range of morpholine-fused triazoles of chemotherapeutic value. The structure of all developed compounds has been elucidated using IR. NMR, MS, and elemental analysis, where four of them have been characterized by single-crystal X-ray analysis.