((2R,3S)-3-Methoxymethoxy-2,3-dihydro-furan-2-yl)-methanol | 96761-01-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢呋喃
• 英文名称: ((2R,3S)-3-Methoxymethoxy-2,3-dihydro-furan-2-yl)-methanol
• 英文别名: 1,4-Anhydro-2-deoxy-3-O-(methoxymethyl)-D-erythro-pent-1-enitol；[(2R,3S)-3-(methoxymethoxy)-2,3-dihydrofuran-2-yl]methanol
• CAS: 96761-01-2
• 化学式: C₇H₁₂O₄
• 分子量: 160.17
• InChiKey: PNEDHXNLRHXOLB-NKWVEPMBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ((2R,3S)-3-Methoxymethoxy-2,3-dihydro-furan-2-yl)-methanol 、 (4-Oxo-3-oxa-13-azatetracyclo[7.7.1.02,7.013,17]heptadeca-1(17),2(7),5,8-tetraen-6-yl) trifluoromethanesulfonate 在 palladium diacetate 1,3-双(二苯基膦)丙烷 、 碳酸氢钠 作用下， 以 乙腈 为溶剂， 反应 3.0h， 以79%的产率得到6-[(2R,5R)-5-(hydroxymethyl)-4-(methoxymethoxy)-2,5-dihydrofuran-2-yl]-3-oxa-13-azatetracyclo[7.7.1.02,7.013,17]heptadeca-1(17),2(7),5,8-tetraen-4-one
  参考文献：
  名称：

  Synthesis of a Novel Coumarin C-Riboside as a Photophysical Probe of Oligonucleotide Dynamics

  摘要：

  DOI：

  10.1021/jo980478+
• 作为产物：
  描述：

  1,4-anhydro-2-deoxy-5-O-[(1,1-dimethylethyl)dimethylsilyl]-D-erythro-pent-1-enitol 在 四丁基氟化铵 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 生成 ((2R,3S)-3-Methoxymethoxy-2,3-dihydro-furan-2-yl)-methanol
  参考文献：
  名称：

  Synthesis of a Novel Coumarin C-Riboside as a Photophysical Probe of Oligonucleotide Dynamics

  摘要：

  DOI：

  10.1021/jo980478+

文献信息

• Facile synthesis of 2'-deoxy-3'-keto- and 2'-deoxypseudouridine derivatives and analogues. Palladium(II)-mediated coupling reactions of furanoid glycals
  作者：Jane Chi Ya Cheng、Uli Hacksell、G. Doyle Daves

  DOI：10.1021/jo00366a003

  日期：1986.8
• Palladium-Mediated Coupling Reactions of an Aminosubstituted Heterocycle. Direct Synthesis of C-Nucleosides Related to Adenosine
  作者：Han-Cheng Zhang、Mohamed Brakta、G. Doyle Daves

  DOI：10.1080/15257779508014656

  日期：1995.2

  C-Nucleosides of the pyrazolo[1,5-a]-1,3,5-triazine aglycon system have been prepared by palladium-mediated coupling of 8-iodopyrazolo[1,5-a]-1,3,5-triazines. 4-(N,N'-Diisobutyloxycarbonyl) amino-8-iodopyrazolo [1,5-a]-1,3,5-triazine and the furanoid glycal 1,4-anhydro-2-deoxy-3-O-[(1,1-dimethylethyl)diphenylsilyl]-D-erythro-pent-1-enitol coupled in the presence of catalytic palladium(0) to yield, after desilylation of the intermediate silyl enol ether, a C-glycoside analog of adenosine.
• Synthesis of a Novel Coumarin C-Riboside as a Photophysical Probe of Oligonucleotide Dynamics
  作者：Robert S. Coleman、Mihaela L. Madaras

  DOI：10.1021/jo980478+

  日期：1998.8.1
• Coumarin base-pair replacement as a fluorescent probe of ultrafast DNA dynamics
  作者：Robert S. Coleman、Mark A. Berg、Catherine J. Murphy

  DOI：10.1016/j.tet.2006.12.096

  日期：2007.4

  The design and synthesis of a novel coumarin C-riboside are described, and is based on the well-known photoprobe Coumarin 102. A diastereofacial selective Heck coupling between a furanoid glycal and a coumarin triflate provided a method for glycoside formation. The coumarin C-glycoside was incorporated synthetically into DNA oligomers, and was used to probe ultrafast dynamics of duplex DNA using time-resolved Stokes shift methods. (c) 2007 Published by Elsevier Ltd.