3-O-benzyl-2-deoxy-2-hydroxymethyl-5-O-mesyl-4-mesyloxymethyl-1-α-methyl-D-ribofuranose | 229469-36-7

• 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-2-deoxy-2-hydroxymethyl-5-O-mesyl-4-mesyloxymethyl-1-α-methyl-D-ribofuranose
• 英文别名: [(3S,4R,5S)-4-(hydroxymethyl)-5-methoxy-2-(methylsulfonyloxymethyl)-3-phenylmethoxyoxolan-2-yl]methyl methanesulfonate
• CAS: 229469-36-7
• 化学式: C₁₇H₂₆O₁₀S₂
• 分子量: 454.519
• InChiKey: MHKTXTQATRBLAA-PMPSAXMXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  29
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  151
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  3-O-benzyl-2-deoxy-2-hydroxymethyl-5-O-mesyl-4-mesyloxymethyl-1-α-methyl-D-ribofuranose 在 4-二甲氨基吡啶 、 sodium hydroxide 、 ammonium sulfate 、 四氯化锡 、 sodium hydride 、 六甲基二硅氮烷 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 56.0h， 生成 (1R,3R,4R,8S)-1-acetoxymethyl-8-benzyloxy-3-(uracil-1-yl)-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
• 作为产物：
  描述：

  (2S,3S,4R,5S)-4-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-5-methoxy-3-phenylmethoxyoxolane-2-carbaldehyde 在 sodium hydroxide 、 溶剂黄146 作用下， 以 1,4-二氧六环 、 吡啶 、 水 为溶剂， 反应 50.75h， 生成 3-O-benzyl-2-deoxy-2-hydroxymethyl-5-O-mesyl-4-mesyloxymethyl-1-α-methyl-D-ribofuranose
  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 Nucleoside Analogs. Synthesis of 2′-Deoxy-2′-C, 4′-C-Bridged Bicyclic Nucleosides
  作者：Guangyi Wang、Esmir Gunic

  DOI：10.1080/15257779908041488

  日期：1999.4

  1-alpha-Methylarabinose was converted, in three steps, to 2-deoxy-2-methyleneribose derivative 3, which was subjected to hydroboration to give 2-alpha-hydroxymethyl derivative 4 exclusively; 4 was converted to 2,4-bis(hydroxymethyl)ribose derivative 6 in four steps. Mesylation, detritylation, and ring closure, followed by hydrolysis of the mesyl group at O5, gave 3,6-dioxabicyclo[3,2,1]octane derivative 8. After acetylation, 8 was coupled with silylated 6-chloropurine to give desired alpha- and beta-bicyclic-sugar nucleosides.
• Conformationally locked nucleosides. Synthesis and stereochemical assignments of 2′-C,4′-C-bridged bicyclonucleosides
  作者：Guangyi Wang、Jean-Luc Girardet、Esmir Gunic

  DOI：10.1016/s0040-4020(99)00394-4

  日期：1999.6

  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.