methyl 3,5-di-O-benzyl-2-C-β-vinyl-α-D-ribofuranoside

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 3,5-di-O-benzyl-2-C-β-vinyl-α-D-ribofuranoside
• 英文别名: (2S,3R,4R,5R)-3-ethenyl-2-methoxy-4-phenylmethoxy-5-(phenylmethoxymethyl)oxolan-3-ol
• 化学式: C₂₂H₂₆O₅
• 分子量: 370.445
• InChiKey: UKHFPRQKCRPZQT-YUMYIRISSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  27
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  甲基 2,3,5-三-O-苄基-D-呋喃核糖苷 在 四氯化锡 、 戴斯-马丁氧化剂 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 94.0h， 生成 methyl 3,5-di-O-benzyl-2-C-β-vinyl-α-D-ribofuranoside
  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

文献信息

• 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.