[(2S,3R,5R)-5-(3-Benzyloxymethyl-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-3-yl]-acetic acid methyl ester | 192564-32-2

• 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: [(2S,3R,5R)-5-(3-Benzyloxymethyl-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-3-yl]-acetic acid methyl ester
• CAS: 192564-32-2
• 化学式: C₃₇H₄₄N₂O₇Si
• 分子量: 656.851
• InChiKey: WBPLKVWECBKNGC-KTCJXSDQSA-N

物化性质

• 沸点：
  683.9±65.0 °C(Predicted)
• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.54
• 重原子数：
  47.0
• 可旋转键数：
  12.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  97.99
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  [(2S,3R,5R)-5-(3-Benzyloxymethyl-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-3-yl]-acetic acid methyl ester 在 正丁基锂 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 43.0h， 生成
  参考文献：
  名称：

  Replacement of the phosphodiester linkage in oligonucleotides by heterocycles: synthesis of thymidine dinucleotide analogs with triazole-modified backbones

  摘要：

  Novel backbone-modified dinucleotide analogs of types V and VI have been synthesized, where the natural phosphodiester linkage of a T-T dinucleotide has been replaced by a triazole heterocycle. The key step of the synthesis is the regioselective, thermal cycloaddition of a 2-oxoalkylidene triphenylphosphorane with an azide derivative to generate the triazole ring. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)00269-2
• 作为产物：
  描述：

  5'-O-(tert-butyldiphenylsilyl)-3'-C-methylenecarboxylic-3'-deoxythymidine 在 4-二甲氨基吡啶 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 8.0h， 生成 [(2S,3R,5R)-5-(3-Benzyloxymethyl-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-3-yl]-acetic acid methyl ester
  参考文献：
  名称：

  Replacement of the phosphodiester linkage in oligonucleotides by heterocycles: synthesis of thymidine dinucleotide analogs with triazole-modified backbones

  摘要：

  Novel backbone-modified dinucleotide analogs of types V and VI have been synthesized, where the natural phosphodiester linkage of a T-T dinucleotide has been replaced by a triazole heterocycle. The key step of the synthesis is the regioselective, thermal cycloaddition of a 2-oxoalkylidene triphenylphosphorane with an azide derivative to generate the triazole ring. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)00269-2