3-O-benzyl-2-deoxy-2-(4,4'-dimethoxytriryloxymethyl)-4-C-hydroxymethyl-1-α-methyl-D-ribofuranose | 229469-35-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 3-O-benzyl-2-deoxy-2-(4,4'-dimethoxytriryloxymethyl)-4-C-hydroxymethyl-1-α-methyl-D-ribofuranose
• 英文别名: [(3S,4R,5S)-4-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-2-(hydroxymethyl)-5-methoxy-3-phenylmethoxyoxolan-2-yl]methanol
• CAS: 229469-35-6
• 化学式: C₃₆H₄₀O₈
• 分子量: 600.709
• InChiKey: GYBNYJXERNXYSB-WKNISULPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  44
• 可旋转键数：
  14
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  95.8
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3-O-benzyl-2-deoxy-2-(4,4'-dimethoxytriryloxymethyl)-4-C-hydroxymethyl-1-α-methyl-D-ribofuranose 在 4-二甲氨基吡啶 、 sodium hydroxide 、 ammonium sulfate 、 四氯化锡 、 sodium hydride 、 溶剂黄146 、 六甲基二硅氮烷 作用下， 以 四氢呋喃 、 吡啶 、 二氯甲烷 、 水 为溶剂， 反应 58.75h， 生成 (1R,3S,4R,8S)-1-acetoxymethyl-8-benzyloxy-3-(thymin-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：

  3-O-benzyl-2-deoxy-2-(4,4'-dimethoxytrityloxymethyl)-1-α-methyl-D-ribofuranose 在 吡啶 、 sodium hydroxide 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 1,4-二氧六环 、 水 、 二甲基亚砜 为溶剂， 反应 55.0h， 生成 3-O-benzyl-2-deoxy-2-(4,4'-dimethoxytriryloxymethyl)-4-C-hydroxymethyl-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 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.