[(2R,3S,5R)-2-[[tert-butyl(diphenyl)silyl]oxymethyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl] (2S)-pyrrolidine-2-carboxylate | 192070-14-7

• 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: [(2R,3S,5R)-2-[[tert-butyl(diphenyl)silyl]oxymethyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl] (2S)-pyrrolidine-2-carboxylate
• CAS: 192070-14-7
• 化学式: C₃₁H₃₉N₃O₆Si
• 分子量: 577.753
• InChiKey: WWGQPXBTTSJTOS-GWMMUDDPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.37
• 重原子数：
  41
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  106
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  [(2R,3S,5R)-2-[[tert-butyl(diphenyl)silyl]oxymethyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl] (2S)-pyrrolidine-2-carboxylate 、 (2S)-2-[(4,5-dimethoxy-2-nitrophenyl)methoxycarbonylamino]-6-[[5-(dimethylamino)naphthalen-1-yl]sulfonylamino]hexanoic acid 在 N-甲基吗啉 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以89%的产率得到3'-O-{N_α-(3,4-dimethoxy-6-nitrobenzyloxycarbonyl)-N_ε-[5-(dimethylamino)-1-naphthalenesulfonyl]-L-lysine-L-proline}-5'O-(tert-butyldiphenylsilyl)thymidine
  参考文献：
  名称：

  An Approach to Photolabile, Fluorescent Protecting Groups

  摘要：

  The photolabile and fluorescent system 1 was prepared via a convergent route which involved thymidine 3'-functionalized with a proline residue. Photodecomposition of 1 was examined using 360 nm irradiation. Without any additives, 5'-silylated thymidine was not formed, but the N-alpha-deprotected cyclization precursor II accumulated instead. However, in the presence of ethanolamine, 5'-silylated thymidine formed at a rate which increases with the concentration of ethanolamine.

  DOI：

  10.1021/jo9702608
• 作为产物：
  描述：

  5'-O-tert-butyldiphenylsilylthymidine 在 N-甲基吗啉 、 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 13.0h， 生成 [(2R,3S,5R)-2-[[tert-butyl(diphenyl)silyl]oxymethyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl] (2S)-pyrrolidine-2-carboxylate
  参考文献：
  名称：

  An Approach to Photolabile, Fluorescent Protecting Groups

  摘要：

  The photolabile and fluorescent system 1 was prepared via a convergent route which involved thymidine 3'-functionalized with a proline residue. Photodecomposition of 1 was examined using 360 nm irradiation. Without any additives, 5'-silylated thymidine was not formed, but the N-alpha-deprotected cyclization precursor II accumulated instead. However, in the presence of ethanolamine, 5'-silylated thymidine formed at a rate which increases with the concentration of ethanolamine.

  DOI：

  10.1021/jo9702608

文献信息

• An Approach to Photolabile, Fluorescent Protecting Groups
  作者：Kevin Burgess、Swanee E. Jacutin、Dongyeol Lim、Aroonsiri Shitangkoon

  DOI：10.1021/jo9702608

  日期：1997.7.1

  The photolabile and fluorescent system 1 was prepared via a convergent route which involved thymidine 3'-functionalized with a proline residue. Photodecomposition of 1 was examined using 360 nm irradiation. Without any additives, 5'-silylated thymidine was not formed, but the N-alpha-deprotected cyclization precursor II accumulated instead. However, in the presence of ethanolamine, 5'-silylated thymidine formed at a rate which increases with the concentration of ethanolamine.