3'-O-{N_α-(3,4-dimethoxy-6-nitrobenzyloxycarbonyl)-N_ε-[5-(dimethylamino)-1-naphthalenesulfonyl]-L-lysine-L-proline}-5'O-(tert-butyldiphenylsilyl)thymidine | 192070-12-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 3'-O-{N_α-(3,4-dimethoxy-6-nitrobenzyloxycarbonyl)-N_ε-[5-(dimethylamino)-1-naphthalenesulfonyl]-L-lysine-L-proline}-5'O-(tert-butyldiphenylsilyl)thymidine
• 英文别名: [(2R,3S,5R)-2-[[tert-butyl(diphenyl)silyl]oxymethyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl] (2S)-1-[(2S)-2-[(4,5-dimethoxy-2-nitrophenyl)methoxycarbonylamino]-6-[[5-(dimethylamino)naphthalen-1-yl]sulfonylamino]hexanoyl]pyrrolidine-2-carboxylate
• CAS: 192070-12-5
• 化学式: C₅₉H₇₁N₇O₁₅SSi
• 分子量: 1178.4
• InChiKey: UILLZXJTKXLEQG-KLTMGZNYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  83
• 可旋转键数：
  25
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  275
• 氢给体数：
  3
• 氢受体数：
  17

反应信息

• 作为反应物：
  描述：

  3'-O-{N_α-(3,4-dimethoxy-6-nitrobenzyloxycarbonyl)-N_ε-[5-(dimethylamino)-1-naphthalenesulfonyl]-L-lysine-L-proline}-5'O-(tert-butyldiphenylsilyl)thymidine 在 C.I.酸性橙108 作用下， 以 水 、 乙腈 为溶剂， 反应 0.5h， 生成 5'-O-tert-butyldiphenylsilylthymidine 、 、 N-[4-[(3S,8aS)-1,4-dioxo-2,3,6,7,8,8a-hexahydropyrrolo[1,2-a]pyrazin-3-yl]butyl]-5-(dimethylamino)naphthalene-1-sulfonamide
  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：

  N-alpha-叔丁氧羰基-L-赖氨酸 在 N-甲基吗啉 、 碳酸氢钠 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 三氟乙酸 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 38.0h， 生成 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

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.