5-O-benzyl-1,2-O-isopropylidene-3-O-propargyl-α-D-xylo-furanose | 1612222-32-8

• 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: 5-O-benzyl-1,2-O-isopropylidene-3-O-propargyl-α-D-xylo-furanose
• 英文别名: (3aR,5R,6S,6aR)-2,2-dimethyl-5-(phenylmethoxymethyl)-6-prop-2-ynoxy-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxole
• CAS: 1612222-32-8
• 化学式: C₁₈H₂₂O₅
• 分子量: 318.37
• InChiKey: QUWFDMSVQHQIRJ-YYIAUSFCSA-N

物化性质

• 沸点：
  429.6±45.0 °C(predicted)
• 密度：
  1.18±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  23.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  46.15
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  5-O-benzyl-1,2-O-isopropylidene-3-O-propargyl-α-D-xylo-furanose 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
  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：

  1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 在 sodium periodate 、 水 、 sodium hydride 、 溶剂黄146 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 、 paraffin oil 为溶剂， 反应 32.5h， 生成 5-O-benzyl-1,2-O-isopropylidene-3-O-propargyl-α-D-xylo-furanose
  参考文献：
  名称：

  单击启发合成1,2,3-三唑连接的1,3,4-恶二唑糖共轭物

  摘要：

  通过Cu（I）催化的叠氮化物-炔烃环加成反应描述了具有生物学优势的1,3,4-恶二唑支架的糖缀合。使用叠氮化物官能化的1,3,4-恶二唑，通过单击化学处理，将从叠氮化物官能化的1,3,4-恶二唑中得到的一系列糖基炔1b – i，以高收率获得三唑连接的糖基化的1,3,4-恶二唑10b – i。已通过广泛的光谱分析（1 H和13 C NMR，IR和MS）确定了开发的糖缀合物的结构。

  DOI：

  10.1002/jhet.2845

文献信息

• 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。
• One-Pot Synthesis of Glycosyl-β-azido Ester via Diazotransfer Reaction Toward Access of Glycosyl-β-triazolyl Ester
  作者：Amrita Mishra、Vinod K. Tiwari

  DOI：10.1021/acs.joc.5b00179

  日期：2015.5.15

  A concise and efficacious one-pot protocol for the synthesis of novel glycosyl-beta-azido ester 3 from glycosyl olefinic ester 1 under mild conditions has been devised. The beta-aminoester, formed by the conjugate addition of ammonia on olefinic ester, undergoes a metal-catalyzed diazotransfer reaction to furnish glycosyl-beta-azido ester. The optimized conditions for diazotransfer reaction indicate that imidazole-1-sulphonyl azide and K2CO3 give the best results in the presence of ZnCl2. A diverse range of novel regioselective triazolyl glycoconjugates 6a-u have been achieved in high yields via 1,3-dipolar cycloaddition of compound 3 with various alkynes in the presence of Cul/DIPEA. Structures of all the compounds have been elucidated using IR, NMR, MS, and elemental analysis, and four of them (3a, 3b, 4b, and 6a) have also been characterized by single crystal X-ray diffraction analysis.
• Efficient synthesis of ethisterone glycoconjugate via bis-triazole linkage
  作者：Kunj B. Mishra、Bhuwan B. Mishra、Vinod K. Tiwari

  DOI：10.1016/j.carres.2014.09.001

  日期：2014.11

  Synthesis of sugar based triazolyl azido-alcohols was accomplished via one pot click reaction of glycosyl alkynes with epichlorohydrin in aqueous medium. All the developed triazolyl azido-alcohols were further utilized for the synthesis of bis-triazolyl ethisterone glycoconjugates using CuAAC reaction. The developed triazole-linked ethisterone glycoconjugates would be crucial in androgen receptor pharmacology and chemical biology. (C) 2014 Elsevier Ltd. All rights reserved.