1-[(2R,4S,5R)-4-[tert-butyl(dimethyl)silyl]oxy-5-[[tert-butyl(dimethyl)silyl]oxymethyl]oxolan-2-yl]-4-(chloro(15N)amino)pyrimidin-2-one | 1133959-37-1

• 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: 1-[(2R,4S,5R)-4-[tert-butyl(dimethyl)silyl]oxy-5-[[tert-butyl(dimethyl)silyl]oxymethyl]oxolan-2-yl]-4-(chloro(15N)amino)pyrimidin-2-one
• CAS: 1133959-37-1
• 化学式: C₂₁H₄₀ClN₃O₄Si₂
• 分子量: 491.184
• InChiKey: FODXBOGDQGQPDF-MUXIBIQHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.51
• 重原子数：
  31
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  72.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  [4-15N]-3',5'-O-bis(tert-butyldimethylsilyl)-2'-deoxycytidine 在 1,3-二氯-5,5-二甲基海因 作用下， 以 二氯甲烷 为溶剂， 反应 0.17h， 以93%的产率得到1-[(2R,4S,5R)-4-[tert-butyl(dimethyl)silyl]oxy-5-[[tert-butyl(dimethyl)silyl]oxymethyl]oxolan-2-yl]-4-(chloro(15N)amino)pyrimidin-2-one
  参考文献：
  名称：

  Introduction of 3′-Terminal Nucleosides Having a Silyl-Type Linker into Polymer Supports without Base Protection

  摘要：

  New 3'-terminal deoxyribonucleoside-loading reagents having a silyl-type linker were developed. They were effectively introduced into polymer supports under the conditions of Huisgen [3 + 2] cycloaddition without base protection. Moreover, four unmodified DNA oligomers d[TACCTAAATCCAX] (X = T, A, C, and A) and a base-labile modified DNA 12mer d[A*C*T*C*C*GT*C*T*A*C*G] 16 (A* = 6-N-acetyl-8-aza-7-deaza-2'-deoxyadenosine, C* = 4-N-acetyl-2'-deoxyctydine, T* = 2-thio-T) were successfully synthesized by cleavage of the silyl-type linker using Bu4NF under neutral conditions in our N-unprotected phosphoramidite method. In this paper, we also report a new reaction of chlorination of cytosine base using 1,3-dichloro-5,5-dimethylhydantoin.

  DOI：

  10.1021/jo9000965

文献信息

• Introduction of 3′-Terminal Nucleosides Having a Silyl-Type Linker into Polymer Supports without Base Protection
  作者：Akihiro Ohkubo、Yasuhiro Noma、Katsufumi Aoki、Hirosuke Tsunoda、Kohji Seio、Mitsuo Sekine

  DOI：10.1021/jo9000965

  日期：2009.4.3

  New 3'-terminal deoxyribonucleoside-loading reagents having a silyl-type linker were developed. They were effectively introduced into polymer supports under the conditions of Huisgen [3 + 2] cycloaddition without base protection. Moreover, four unmodified DNA oligomers d[TACCTAAATCCAX] (X = T, A, C, and A) and a base-labile modified DNA 12mer d[A*C*T*C*C*GT*C*T*A*C*G] 16 (A* = 6-N-acetyl-8-aza-7-deaza-2'-deoxyadenosine, C* = 4-N-acetyl-2'-deoxyctydine, T* = 2-thio-T) were successfully synthesized by cleavage of the silyl-type linker using Bu4NF under neutral conditions in our N-unprotected phosphoramidite method. In this paper, we also report a new reaction of chlorination of cytosine base using 1,3-dichloro-5,5-dimethylhydantoin.