[(2R,3S,4R)-4-hydroxy-2-(2-hydroxyethyl)-5-methoxyoxolan-3-yl]methyl benzoate | 441044-21-9

• 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: [(2R,3S,4R)-4-hydroxy-2-(2-hydroxyethyl)-5-methoxyoxolan-3-yl]methyl benzoate
• CAS: 441044-21-9
• 化学式: C₁₅H₂₀O₆
• 分子量: 296.32
• InChiKey: PPNKHQJFTPGLLA-OSBVZDBCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  85.2
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  [(2R,3S,4R)-4-hydroxy-2-(2-hydroxyethyl)-5-methoxyoxolan-3-yl]methyl benzoate 在 4-二甲氨基吡啶 吡啶 、 偶氮二异丁腈 、 acidic cation-exchange resin (Dowex 50 W₈) 、 三正丁基氢锡 作用下， 以 甲苯 为溶剂， 反应 4.25h， 生成 (1R,5R,6R)-6-<(benzoyloxy)methyl>-2,8-dioxabicyclo-<3.2.1>octane
  参考文献：
  名称：

  Building blocks for oligonucleotide analogs with dimethylene sulfide, sulfoxide, and sulfone groups replacing phosphodiester linkages

  摘要：

  Two routes are presented for the synthesis of 3',5'-bishomodeoxyribonucleosides, building blocks needed to synthesize oligodeoxynucleotide analogues where the OPO2O groups are replaced by CH2SCH2, CH2SOCH2, and CH2SO2CH2 units. Two of these have been coupled to create an uncharged analogue of a dinucleotide. As isosteric, achiral, and nonionic analogues of natural oligonucleotides stable to both enzymatic and chemical hydrolysis, such molecules have potential application as probes in the laboratory, in studies of the role of individual genes in biological function, and as ''antisense'' oligonucleotide analogues for the treatment of diseases.

  DOI：

  10.1021/jo00012a018
• 作为产物：
  描述：

  ((3aR,5S,6R,6aR)-tetrahydro-2,2-dimethyl-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)furo[2,3-d][1,3]dioxol-6-yl)methanol 在 4-二甲氨基吡啶 吡啶 、 dimethyl sulfide borane 、 acidic cation-exchange resin (Dowex 50 W₈) 、 硫酸 、 双氧水 、 碳酸氢钠 、 sodium iodide 作用下， 以 甲醇 、 氯仿 、 丁酮 为溶剂， 反应 156.5h， 生成 [(2R,3S,4R)-4-hydroxy-2-(2-hydroxyethyl)-5-methoxyoxolan-3-yl]methyl benzoate
  参考文献：
  名称：

  Building blocks for oligonucleotide analogs with dimethylene sulfide, sulfoxide, and sulfone groups replacing phosphodiester linkages

  摘要：

  Two routes are presented for the synthesis of 3',5'-bishomodeoxyribonucleosides, building blocks needed to synthesize oligodeoxynucleotide analogues where the OPO2O groups are replaced by CH2SCH2, CH2SOCH2, and CH2SO2CH2 units. Two of these have been coupled to create an uncharged analogue of a dinucleotide. As isosteric, achiral, and nonionic analogues of natural oligonucleotides stable to both enzymatic and chemical hydrolysis, such molecules have potential application as probes in the laboratory, in studies of the role of individual genes in biological function, and as ''antisense'' oligonucleotide analogues for the treatment of diseases.

  DOI：

  10.1021/jo00012a018

文献信息

• Oligodeoxyribonucleotide Analogues with Bridging Dimethylene Sulfide, Sulfoxide, and Sulfone Groups. Toward a Second-Generation Model of Nucleic Acid Structure
  作者：Zhen Huang、Steven A. Benner

  DOI：10.1021/jo0003910

  日期：2002.6.1

  Short DNA analogues with bridging dimethylene sulfide, sulfoxide, and sulfone groups replacing the phosphate diesters (S-DNAs) were synthesized from building blocks prepared via two routes, both starting from D-glucose. Building blocks for RNA analogues were prepared by stereoselective introduction of nucleobase into a 2'-acylated ribose analogue. The ribose analogues were converted to deoxyribose

  由桥接二甲基硫醚，亚砜和砜基取代磷酸二酯（S-DNA）的短DNA类似物是从通过两种途径制备的结构单元合成的，均从D-葡萄糖开始。通过将核碱基立体选择性地引入2'-酰化的核糖类似物中来制备RNA类似物的构件。通过用硫代乙酰基单元取代3''-OH基团，然后进行光解脱氧或基于自由基的2'-脱氧，将核糖类似物转化为脱氧核糖类似物。通过CH（2）（-）S-CH（2）单元连接的DNA类似物是通过S（N）2置换一个构件上的6'-甲磺酰基使用另一构件的硫醇盐亲核试剂制备的。建立了巯基和羟基的4,4'-二甲氧基三苯甲基保护和脱保护方案。通过用过氧化氢氧化获得相应的亚砜DNA类似物。在硅酸钛催化剂存在下，用过硫酸盐或过氧化氢将硫化物DNA氧化，即可得到砜DNA类似物。检查了几种代表性寡核苷酸类似物的物理性质，并根据DNA链识别的“第二代”模型进行了解释，该模型强调了聚阴离子主链在减少高度官能化分子形成的不良趋
• Nonionic Analogs of RNA with Dimethylene Sulfone Bridges
  作者：Clemens Richert、Andrew L. Roughton、Steven A. Benner

  DOI：10.1021/ja952322m

  日期：1996.1.1

  Analogs of RNA have been synthesized where each of the phosphodiester linking groups is replaced by dimethylene sulfone units (sulfone-linked nucleic acid analogs of RNA, or “rSNAs”). These are the...

  已经合成了 RNA 类似物，其中每个磷酸二酯连接基团都被二亚甲基砜单元（RNA 的砜连接的核酸类似物，或“rSNA”）取代。这些是...