3'-O-(tert-butyldimethylsilyl)thymidin-5'-yl methyl phosphonate | 161790-66-5

• 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: 3'-O-(tert-butyldimethylsilyl)thymidin-5'-yl methyl phosphonate
• 英文别名: 3'-O-(t-butyldimethylsilyl)-5'-O-(H-methylphosphonyl)thymidine；1-[(2R,4S,5R)-4-[tert-butyl(dimethyl)silyl]oxy-5-[[methoxy(oxido)phosphaniumyl]oxymethyl]oxolan-2-yl]-5-methylpyrimidine-2,4-dione
• CAS: 161790-66-5
• 化学式: C₁₇H₃₁N₂O₇PSi
• 分子量: 434.502
• InChiKey: GBCYIAJXTIWEAB-BFHYXJOUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.51
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  109
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3'-O-(tert-butyldimethylsilyl)thymidin-5'-yl methyl phosphonate 以 二氯甲烷 为溶剂， 反应 0.75h， 生成 1-[(2R,4S,5R)-4-[tert-butyl(dimethyl)silyl]oxy-5-[[methoxy-[(2R,3S,5R)-2-[[(4-methoxyphenyl)-diphenylmethoxy]methyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]sulfanylphosphoryl]oxymethyl]oxolan-2-yl]-5-methylpyrimidine-2,4-dione
  参考文献：
  名称：

  Li, Xiang; Scott, Gerard K.; Baxter, Anthony D., Journal of the Chemical Society. Perkin transactions I, 1994, # 15, p. 2123 - 2130

  摘要：

  DOI：
• 作为产物：
  描述：

  3'-O-(叔丁基二甲基硅烷基)胸苷 在 四氮唑 、 N,N-二异丙基乙胺 作用下， 以 水 、 乙腈 为溶剂， 反应 1.0h， 生成 3'-O-(tert-butyldimethylsilyl)thymidin-5'-yl methyl phosphonate
  参考文献：
  名称：

  Conformationally Locked Nucleosides. Synthesis of Oligodeoxynucleotides Containing 3′-Amino-3′-deoxy-3′-N,5′(R)-C-ethylenethymidine

  摘要：

  3'-Amino-3'-deoxy-5'-O-(4,4'-dimethoxytrityl)-3'-N,5(R)-C-ethylenethymidine (6)was synthesized starting from 3'-azido-3'-deoxythymidine. Condensation of 6 with 5'-O-(H-phosphonyl)thymidine and 5'-O-(p-nitrophenoxycarbonyl)thymidine derivatives gave dinucleotide and dinucleoside derivatives, respectively, which were incorporated into oligodeoxynucleotides (ODNs). Tm data of the modified ODNs are also presented.

  DOI：

  10.1080/15257770008033851

文献信息

• Synthesis and properties of 3′-amino-2′,4′-BNA, a bridged nucleic acid with a N3′→P5′ phosphoramidate linkage
  作者：Satoshi Obika、S.M. Abdur Rahman、Bingbing Song、Mayumi Onoda、Makoto Koizumi、Koji Morita、Takeshi Imanishi

  DOI：10.1016/j.bmc.2008.09.013

  日期：2008.10

  The synthesis and properties of a bridged nucleic acid analogue containing a N3'-->P5' phosphoramidate linkage, 3'-amino-2',4'-BNA, is described. A heterodimer containing a 3'-amino-2',4'-BNA thymine monomer, and thymine and methylcytosine monomers of 3'-amino-2',4'-BNA and their 5'-phosphoramidites, were synthesized efficiently. The dimer and monomers were incorporated into oligonucleotides by conventional

  描述了包含N3'-> P5'氨基磷酸酯键3'-氨基-2'，4'-BNA的桥接核酸类似物的合成和性质。有效地合成了包含3'-氨基-2'，4'-BNA胸腺嘧啶单体以及3'-氨基-2'，4'-BNA的胸腺嘧啶和甲基胞嘧啶单体及其5'-亚磷酰胺的异二聚体。通过常规的3'-> 5'组装和5'-> 3'反向组装亚磷酰胺方案分别将二聚体和单体掺入寡核苷酸。与天然DNA寡核苷酸相比，含有3'-氨基-2'，4'-BNA残基的修饰寡核苷酸与单链DNA（ssDNA），单链RNA（ssRNA）和双链DNA形成高度稳定的双链体和三链体。链DNA（dsDNA）靶标，相对于ssDNA，ssRNA和dsDNA的平均解链温度（T（m））分别为+2.7到+4.0摄氏度，+ 5.0到+7.0摄氏度和+5.0到+11.0摄氏度。这些增加与2'，4'-BNA修饰的寡核苷酸观察到的增加相当。此外，用单个3'-氨基-2'，4'-BNA
• Li, Xiang; Scott, Gerard K.; Baxter, Anthony D., Journal of the Chemical Society. Perkin transactions I, 1994, # 15, p. 2123 - 2130
  作者：Li, Xiang、Scott, Gerard K.、Baxter, Anthony D.、Taylor, Roger J.、Vyle, Joseph S.、Cosstick, Richard

  DOI：——

  日期：——
• Conformationally Locked Nucleosides. Synthesis of Oligodeoxynucleotides Containing 3′-Amino-3′-deoxy-3′-N,5′(R)-C-ethylenethymidine
  作者：Guangyi Wang、Vesna Stoisavljevic

  DOI：10.1080/15257770008033851

  日期：2000.9

  3'-Amino-3'-deoxy-5'-O-(4,4'-dimethoxytrityl)-3'-N,5(R)-C-ethylenethymidine (6)was synthesized starting from 3'-azido-3'-deoxythymidine. Condensation of 6 with 5'-O-(H-phosphonyl)thymidine and 5'-O-(p-nitrophenoxycarbonyl)thymidine derivatives gave dinucleotide and dinucleoside derivatives, respectively, which were incorporated into oligodeoxynucleotides (ODNs). Tm data of the modified ODNs are also presented.