(1R,3S,4R,8S)-1-acetoxymethyl-8-benzyloxy-3-methoxy-2,6-dioxabicyclo<3.2.1>octane | 226214-51-3

• 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: (1R,3S,4R,8S)-1-acetoxymethyl-8-benzyloxy-3-methoxy-2,6-dioxabicyclo<3.2.1>octane
• 英文别名: [(1R,5R,7S,8S)-7-methoxy-8-phenylmethoxy-3,6-dioxabicyclo[3.2.1]octan-5-yl]methyl acetate
• CAS: 226214-51-3
• 化学式: C₁₇H₂₂O₆
• 分子量: 322.358
• InChiKey: OGTWUAADEQWFSU-LTIDMASMSA-N

物化性质

• 沸点：
  423.3±45.0 °C(Predicted)
• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (1R,3S,4R,8S)-1-acetoxymethyl-8-benzyloxy-3-methoxy-2,6-dioxabicyclo<3.2.1>octane 在 吡啶 、 ammonium sulfate 、 三氯化硼 、 四氯化锡 、 六甲基二硅氮烷 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 10.0h， 生成 Acetic acid (1R,5R,7R,8S)-5-acetoxymethyl-7-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3,6-dioxa-bicyclo[3.2.1]oct-8-yl ester
  参考文献：
  名称：

  Conformationally locked nucleosides. Synthesis and stereochemical assignments of 2′-C,4′-C-bridged bicyclonucleosides

  摘要：

  1-alpha-O-Methyl-3-O,5-O-TIPDS-arabinose was converted, in multiple steps, to 2,6-dioxabicyclo[3,2,1]octane derivatives, which were condensed with silylated nucleoside bases to give the desired 2',4'-bridged bicyclonucleosides. In this article, synthesis and stereochemical assignments of the bicyclonucleosides are described. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00394-4
• 作为产物：
  描述：

  methyl 3,5-O-(tetraisopropylsiloxane-1,3-diyl)-α-D-arabinofuranoside 在 吡啶 、 4-二甲氨基吡啶 、 sodium perborate 、 sodium hydroxide 、 9-borabicyclo[3.3.1]nonane dimer 、 四丁基氟化铵 、 草酸 、 sodium tert-pentoxide 、 sodium hydride 、 溶剂黄146 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 吡啶 、 乙醚 、 二氯甲烷 、 水 、 二甲基亚砜 、 苯 为溶剂， 反应 150.25h， 生成 (1R,3S,4R,8S)-1-acetoxymethyl-8-benzyloxy-3-methoxy-2,6-dioxabicyclo<3.2.1>octane
  参考文献：
  名称：

  Conformationally locked nucleosides. Synthesis and stereochemical assignments of 2′-C,4′-C-bridged bicyclonucleosides

  摘要：

  1-alpha-O-Methyl-3-O,5-O-TIPDS-arabinose was converted, in multiple steps, to 2,6-dioxabicyclo[3,2,1]octane derivatives, which were condensed with silylated nucleoside bases to give the desired 2',4'-bridged bicyclonucleosides. In this article, synthesis and stereochemical assignments of the bicyclonucleosides are described. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00394-4

文献信息

• Conformationally locked nucleosides. Synthesis and hybridization properties of oligodeoxynucleotides containing 2′,4′-C-bridged 2′-deoxynucleosides
  作者：Guangyi Wang、Esmir Gunic、Jean-Luc Girardet、Vesna Stoisavljevic

  DOI：10.1016/s0960-894x(99)00146-8

  日期：1999.4

  A conformationally locked, 2',4'-C-bridged 2'-deoxyribofuranoside2 was condensed with silylated pyrimidines to give 2',4'-C-bridged bicyclonucleosides, which were converted to the phosphoramidites and incorporated into oligodeoxynucleotides (ODNs). The hybridization data of the modified ODNs to DNA and RNA are presented.

  将构象锁定的2'，4'-C桥连的2'-脱氧核糖呋喃糖苷2与甲硅烷基化的嘧啶缩合，得到2'，4'-C桥连的双环核苷，将其转化为亚磷酰胺并掺入寡脱氧核苷酸（ODN）。显示了修饰的ODN与DNA和RNA的杂交数据。