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 | 1341219-71-3

• 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: 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
• 英文别名: (E)-N-[[4-[tert-butyl(dimethyl)silyl]oxy-2-methoxyphenyl]methyl]-3-[(2R,3R,4R,5R)-4-[tert-butyl(dimethyl)silyl]oxy-3-prop-2-enoxy-5-[6-(tritylamino)purin-9-yl]oxolan-2-yl]-N-[4-methoxy-2,5-bis(methoxymethoxy)-3-prop-2-enylphenyl]prop-2-enamide
• CAS: 1341219-71-3
• 化学式: C₆₈H₈₆N₆O₁₁Si₂
• 分子量: 1219.64
• InChiKey: WNYQNEBGRAINTF-MUVVRZPQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.97
• 重原子数：
  87
• 可旋转键数：
  30
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  168
• 氢给体数：
  1
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  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 在 Grubbs catalyst first generation 、 三乙基硅烷 、 palladium 10% on activated carbon 、 四丁基氟化铵 、 水 、 cesium fluoride 、 三氟乙酸 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 二氯甲烷 为溶剂， 反应 30.0h， 生成 (4E,6R,8R,9R,10S,13Z)-8-(6-aminopurin-9-yl)-9-hydroxy-17-methoxy-7,11-dioxa-2-azatricyclo[14.3.1.06,10]icosa-1(19),4,13,16-tetraene-3,18,20-trione
  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：

  (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

文献信息

• Development of the Carboxamide Protecting Group, 4-(<i>tert</i>-Butyldimethylsiloxy)-2-methoxybenzyl
  作者：Kazuhiro Muranaka、Satoshi Ichikawa、Akira Matsuda

  DOI：10.1021/jo201495w

  日期：2011.11.18

  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.