methyl 2,3,5-tri-O-(4-chlorobenzyl)-β-D-ribofuranoside | 108008-65-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,3,5-tri-O-(4-chlorobenzyl)-β-D-ribofuranoside
• 英文别名: (2R,3R,4R,5R)-3,4-bis[(4-chlorophenyl)methoxy]-2-[(4-chlorophenyl)methoxymethyl]-5-methoxyoxolane
• CAS: 108008-65-7
• 化学式: C₂₇H₂₇Cl₃O₅
• 分子量: 537.867
• InChiKey: GZQPNZGZTBZMHW-FPCALVHFSA-N

物化性质

• 沸点：
  613.1±55.0 °C(Predicted)
• 密度：
  1.33±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  35
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  46.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 2,3,5-tri-O-(4-chlorobenzyl)-β-D-ribofuranoside 在 四氯化锡 作用下， 以 二氯甲烷 为溶剂， 反应 36.0h， 以83%的产率得到甲基3,5-二-O-(4-氯苄基)-Α-D-呋喃呋喃糖苷
  参考文献：
  名称：

  Efficient Synthesis of Methyl 3,5-Di-O-benzyl-α-d-ribofuranoside and Application to the Synthesis of 2‘-C-β-Alkoxymethyluridines

  摘要：

  Methyl 3,5-di-O-arylmethyl-alpha-D-ribofuranosides have been used extensively as synthons to construct 2'-C-branched ribonucleosides. Herein, we describe efficient access to methyl 3,5-di-O-arylmethyl-alpha-D-ribofuranosides (aryl: 2-ClC6H4, 3-ClC6H4, 4-ClC6H4, 4-BrC6H4, 2,4-Cl2C6H3, Ph) in 72-82% yields from methyl D-ribofuranoside. We also demonstrate efficient access to the versatile precursor methyl 3,5-di-O-benzyl-alpha-D-ribofuranoside (3f) and the synthesis of 2'-C-beta-methoxymethyl- and 2'-C-beta-ethoxymethyluridine in six steps from 3f with overall yields of 18% and 32%, respectively.

  DOI：

  10.1021/ol071075b
• 作为产物：
  描述：

  α,β-1-甲基-D-呋喃核糖苷 、 4-氯氯苄 在 sodium hydride 、 二甲基亚砜 作用下， 生成 methyl 2,3,5-tri-O-(4-chlorobenzyl)-β-D-ribofuranoside
  参考文献：
  名称：

  An efficient synthesis of partially protected .alpha.-D-ribofuranosides from D-ribose by way of a unique selective debenzylation reaction

  摘要：

  DOI：

  10.1021/jo00389a049

文献信息

• 2′-Deoxy-2′-α-C-(hydroxymethyl)adenosine as Potential anti-HCV Agent
  作者：Natascha Chavain、Piet Herdewijn

  DOI：10.1002/ejoc.201001448

  日期：2011.2

  Because of the importance of C-branched nucleosides in the discovery of new antiviral molecules, we decided to synthesize 2-deoxy-2-α-C-(hydroxymethyl)adenosine as a potential anti-HCV agent. The synthesis of a new adenosine ana

  由于 C-分支核苷在发现新的抗病毒分子中的重要性，我们决定合成 2-脱氧-2-α-C-（羟甲基）腺苷作为潜在的抗 HCV 药物。一种新型腺苷酸的合成
• Efficient Synthesis of Methyl 3,5-Di-<i>O</i>-benzyl-α-<scp>d</scp>-ribofuranoside and Application to the Synthesis of 2‘-<i>C</i>-β-Alkoxymethyluridines
  作者：Nan-Sheng Li、Jun Lu、Joseph A. Piccirilli

  DOI：10.1021/ol071075b

  日期：2007.8.1

  Methyl 3,5-di-O-arylmethyl-alpha-D-ribofuranosides have been used extensively as synthons to construct 2'-C-branched ribonucleosides. Herein, we describe efficient access to methyl 3,5-di-O-arylmethyl-alpha-D-ribofuranosides (aryl: 2-ClC6H4, 3-ClC6H4, 4-ClC6H4, 4-BrC6H4, 2,4-Cl2C6H3, Ph) in 72-82% yields from methyl D-ribofuranoside. We also demonstrate efficient access to the versatile precursor methyl 3,5-di-O-benzyl-alpha-D-ribofuranoside (3f) and the synthesis of 2'-C-beta-methoxymethyl- and 2'-C-beta-ethoxymethyluridine in six steps from 3f with overall yields of 18% and 32%, respectively.
• An efficient synthesis of partially protected .alpha.-D-ribofuranosides from D-ribose by way of a unique selective debenzylation reaction
  作者：Olivier R. Martin、Kenneth G. Kurz、S. P. Rao

  DOI：10.1021/jo00389a049

  日期：1987.6