N-(3-allyl-4-methoxy-2,5-bis-methoxymethoxyphenyl)-N-(4-tert-butyldimethylsiloxy-2-methoxybenzyl)diethylphosphonoacetamide | 1341219-64-4

• 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: N-(3-allyl-4-methoxy-2,5-bis-methoxymethoxyphenyl)-N-(4-tert-butyldimethylsiloxy-2-methoxybenzyl)diethylphosphonoacetamide
• 英文别名: N-[[4-[tert-butyl(dimethyl)silyl]oxy-2-methoxyphenyl]methyl]-2-diethoxyphosphoryl-N-[4-methoxy-2,5-bis(methoxymethoxy)-3-prop-2-enylphenyl]acetamide
• CAS: 1341219-64-4
• 化学式: C₃₄H₅₄NO₁₁PSi
• 分子量: 711.862
• InChiKey: CYBNHCKFLKMUNB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.58
• 重原子数：
  48
• 可旋转键数：
  22
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  120
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  (2S,3R,4R,5R)-4-[tert-butyl(dimethyl)silyl]oxy-3-prop-2-enoxy-5-[6-(tritylamino)purin-9-yl]oxolane-2-carbaldehyde 、 N-(3-allyl-4-methoxy-2,5-bis-methoxymethoxyphenyl)-N-(4-tert-butyldimethylsiloxy-2-methoxybenzyl)diethylphosphonoacetamide 在 四甲基乙二胺 、 zinc trifluoromethanesulfonate 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 以850 mg的产率得到N-(3-allyl-4-methoxy-2,5-bis-methoxymethoxyphenyl)-N-(4-tert-butyldimethylsiloxy-2-methoxybenzyl) (E)-3-O-allyl-1-(6-amino-N6-trityl-9H-purin-9-yl)-2-O-tert-butyldimethylsilyl-5,6-dideoxy-β-D-ribo-5-eneheptofuranuronamide
  参考文献：
  名称：

  Development of the Carboxamide Protecting Group, 4-(tert-Butyldimethylsiloxy)-2-methoxybenzyl

  摘要：

  The new carboxamide protecting group, 4-(tert-butyldimethylsiloxy)-2-methoxybenzyl (SiMB), has been developed. While this SiMB group can be removed using mild basic desilylation methods, it can also be deprotected under strongly acidic or oxidative conditions. An application of this group to simple carboxamide groups, as well as to more complex and acid-sensitive adenosine derivatives containing a cyclophane scaffold, was also demonstrated.

  DOI：

  10.1021/jo201495w
• 作为产物：
  描述：

  4-羟基-2-甲氧基苯甲醛 在 咪唑 、 三乙酰氧基硼氢化钠 、 溶剂黄146 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.33h， 生成 N-(3-allyl-4-methoxy-2,5-bis-methoxymethoxyphenyl)-N-(4-tert-butyldimethylsiloxy-2-methoxybenzyl)diethylphosphonoacetamide
  参考文献：
  名称：

  Development of the Carboxamide Protecting Group, 4-(tert-Butyldimethylsiloxy)-2-methoxybenzyl

  摘要：

  The new carboxamide protecting group, 4-(tert-butyldimethylsiloxy)-2-methoxybenzyl (SiMB), has been developed. While this SiMB group can be removed using mild basic desilylation methods, it can also be deprotected under strongly acidic or oxidative conditions. An application of this group to simple carboxamide groups, as well as to more complex and acid-sensitive adenosine derivatives containing a cyclophane scaffold, was also demonstrated.

  DOI：

  10.1021/jo201495w