3',5'-di-O-benzyl-2'-C-β-methoxymethyluridine | 948838-17-3

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 3',5'-di-O-benzyl-2'-C-β-methoxymethyluridine
• 英文别名: 1-[(2R,3R,4R,5R)-3-hydroxy-3-(methoxymethyl)-4-phenylmethoxy-5-(phenylmethoxymethyl)oxolan-2-yl]pyrimidine-2,4-dione
• CAS: 948838-17-3
• 化学式: C₂₅H₂₈N₂O₇
• 分子量: 468.507
• InChiKey: XBKJDGIZZVINEO-HBAHCVPVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  34
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  107
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3',5'-di-O-benzyl-2'-C-β-methoxymethyluridine 在 palladium hydroxide - carbon 氢气 作用下， 以 甲醇 为溶剂， 反应 21.0h， 以92%的产率得到2'-C-β-methoxymethyluridine
  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：

  甲基 2,3,5-三-O-苄基-D-呋喃核糖苷 在 4-二甲氨基吡啶 、 sodium hydroxide 、 ammonium sulfate 、 四氯化锡 、 戴斯-马丁氧化剂 、 magnesium 、 三乙胺 、 六甲基二硅氮烷 、 mercury dichloride 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 267.5h， 生成 3',5'-di-O-benzyl-2'-C-β-methoxymethyluridine
  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.