5-amino-3',5'-di-O-(t-butyldimethylsilyl)-2'-deoxyuridine | 145125-16-2

• 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: 5-amino-3',5'-di-O-(t-butyldimethylsilyl)-2'-deoxyuridine
• 英文别名: 5-amino-3',5'-di-O-(tert-butyldimethylsilyl)-2'-deoxyuridine；5-amino-1-[(2R,4S,5R)-4-[tert-butyl(dimethyl)silyl]oxy-5-[[tert-butyl(dimethyl)silyl]oxymethyl]oxolan-2-yl]pyrimidine-2,4-dione
• CAS: 145125-16-2
• 化学式: C₂₁H₄₁N₃O₅Si₂
• 分子量: 471.745
• InChiKey: WTHXOVJFLZSRGM-GVDBMIGSSA-N

物化性质

• 密度：
  1.09±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.82
• 重原子数：
  31
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  103
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5-amino-3',5'-di-O-(t-butyldimethylsilyl)-2'-deoxyuridine 在 5 wt% Rh/Al2O3 、 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、303.99 kPa 条件下， 反应 90.0h， 以70%的产率得到5-amino-3',5'-di-O-(tert-butyldimethylsilyl)-4,5-dihydro-2'-deoxyuridine
  参考文献：
  名称：

  Design and Synthesis of Thalidomide–Deoxyribonucleoside Chimeras

  摘要：

  新合成的沙利度胺脱氧核苷嵌合体可能是安全的沙利度胺类抗肿瘤药物。

  DOI：

  10.1246/cl.2009.1046
• 作为产物：
  描述：

  溴脲苷 在 吡啶 、 氨 作用下， 反应 48.0h， 生成 5-amino-3',5'-di-O-(t-butyldimethylsilyl)-2'-deoxyuridine
  参考文献：
  名称：

  Effect of C5-amino substituent on 2′-deoxyuridine base pairing with 2′-deoxyadenosine: investigation by 1H and 13C NMR spectroscopy

  摘要：

  Substituents at 5-position of a pyrimidine base are known to affect its base pairing properties with complementary purines, either by altering the imino N3-H acidity or by modifying the acceptor strength of C2 and C4 carbonyls. This paper reports comparative base pair property of 5-methyl-2'-deoxyuridine (dT) and 5-amino-2'-deoxyuridine (dUNH2) with 2'-deoxyadenosine (dA) as their 3',5'-di-t-butyldimethylsilyl derivatives in chloroform-d. Using H-1 and C-13 NMR, it is demonstrated that the 5-NH2 substituent in 2'-deoxyuridine results in (i) decreased association (lower K(a)) with 2'-deoxyadenosine compared to dA:dT complexation and (ii) increased receptor strength of C2 carbonyl compared to C4 carbonyl and (iii) lower temperature for separation of 6-amino protons of dA due to its complexation with dUNH2 compared to that with dT.

  DOI：

  10.1016/s0040-4020(01)86598-4

文献信息

• Effect of C5-amino substituent on 2′-deoxyuridine base pairing with 2′-deoxyadenosine: investigation by 1H and 13C NMR spectroscopy
  作者：Dinesh.A. Barawkar、R.Krishna Kumar、K.N. Ganesh

  DOI：10.1016/s0040-4020(01)86598-4

  日期：1992.9

  Substituents at 5-position of a pyrimidine base are known to affect its base pairing properties with complementary purines, either by altering the imino N3-H acidity or by modifying the acceptor strength of C2 and C4 carbonyls. This paper reports comparative base pair property of 5-methyl-2'-deoxyuridine (dT) and 5-amino-2'-deoxyuridine (dUNH2) with 2'-deoxyadenosine (dA) as their 3',5'-di-t-butyldimethylsilyl derivatives in chloroform-d. Using H-1 and C-13 NMR, it is demonstrated that the 5-NH2 substituent in 2'-deoxyuridine results in (i) decreased association (lower K(a)) with 2'-deoxyadenosine compared to dA:dT complexation and (ii) increased receptor strength of C2 carbonyl compared to C4 carbonyl and (iii) lower temperature for separation of 6-amino protons of dA due to its complexation with dUNH2 compared to that with dT.
• Design and Synthesis of Thalidomide–Deoxyribonucleoside Chimeras
  作者：Shigeru Suzuki、Takeshi Yamamoto、Etsuko Tokunaga、Shuichi Nakamura、Motohiro Tanaka、Takuma Sasaki、Norio Shibata

  DOI：10.1246/cl.2009.1046

  日期：2009.11.5

  Novel thalidomide–deoxyribonucleoside chimeras have been synthesized as potentially safe, thalidomide-based antitumour agents.

  新合成的沙利度胺脱氧核苷嵌合体可能是安全的沙利度胺类抗肿瘤药物。