5'-O-(4,4'-dimethoxytrityl)thymidyl-(3'->5')-3'-O-[(ethoxy)diisopropylsilyl]thymidine | 497070-26-5

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷酸
• 英文名称: 5'-O-(4,4'-dimethoxytrityl)thymidyl-(3'->5')-3'-O-[(ethoxy)diisopropylsilyl]thymidine
• 英文别名: [(2R,3S,5R)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl] [(2R,3S,5R)-3-[ethoxy-di(propan-2-yl)silyl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl hydrogen phosphate
• CAS: 497070-26-5
• 化学式: C₄₉H₆₃N₄O₁₅PSi
• 分子量: 1007.12
• InChiKey: SVLAAWZSDMGJEY-LVFDAWRISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.49
• 重原子数：
  70
• 可旋转键数：
  21
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  219
• 氢给体数：
  3
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  5'-O-(4,4'-dimethoxytrityl)thymidyl-(3'->5')-3'-O-[(ethoxy)diisopropylsilyl]thymidine 在 methyl phosphorimidazolide 、 4-nitro-6-(trifluoromethyl)-1H-benzo[d][1,2,3]triazol-1-ol 作用下， 以52%的产率得到DMTrOTpT
  参考文献：
  名称：

  摘要：

  In connection with the synthesis of guanosine-capped of oligodeoxynucleotides on polymer supports, we found an unprecedented Si-O bond cleavage reaction, which occurred when polymer-linked oligodeoxynucleoticles having unprotected internucleotidic phosphate groups were allowed to react with the guanosine 5'-phosphorimidazolide derivative 18 in the presence of 4-nitro-6-(trifluoromethyl)-1H-benzotriazol-1-ol (Ntbt-OH) as an effective activator in pyridine. This side reaction was confirmed by the fact that the liquid-phase reaction of DMTrTpT-O-Si(iPr(2))OEt 42 with a simpler model compound. methyl phosphorimidazolide 34. in the presence of Ntbt-OH gave DMTrTpT 43. It turned out that the side reaction hardly occurs without unprotected internucleotidic phosphate groups on oligodeoxyriucleotides. The detailed study of this side reaction disclosed that Ntbt-OH directly attacks the Si-atom to release oligonucleotides from the resin. It is likely that Ntbt-OH serves as a very strong nucleophile in pyridine, especially to the Si-atom of the linker.

  DOI：

  10.1002/1522-2675(200209)85:9<2930::aid-hlca2930>3.0.co;2-2
• 作为产物：
  描述：

  保护胸苷 在 咪唑 、 四氮唑 、 叔丁基过氧化氢 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 zinc dibromide 作用下， 以 吡啶 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 异丙醇 、 乙腈 为溶剂， 反应 2.5h， 生成 5'-O-(4,4'-dimethoxytrityl)thymidyl-(3'->5')-3'-O-[(ethoxy)diisopropylsilyl]thymidine
  参考文献：
  名称：

  摘要：

  In connection with the synthesis of guanosine-capped of oligodeoxynucleotides on polymer supports, we found an unprecedented Si-O bond cleavage reaction, which occurred when polymer-linked oligodeoxynucleoticles having unprotected internucleotidic phosphate groups were allowed to react with the guanosine 5'-phosphorimidazolide derivative 18 in the presence of 4-nitro-6-(trifluoromethyl)-1H-benzotriazol-1-ol (Ntbt-OH) as an effective activator in pyridine. This side reaction was confirmed by the fact that the liquid-phase reaction of DMTrTpT-O-Si(iPr(2))OEt 42 with a simpler model compound. methyl phosphorimidazolide 34. in the presence of Ntbt-OH gave DMTrTpT 43. It turned out that the side reaction hardly occurs without unprotected internucleotidic phosphate groups on oligodeoxyriucleotides. The detailed study of this side reaction disclosed that Ntbt-OH directly attacks the Si-atom to release oligonucleotides from the resin. It is likely that Ntbt-OH serves as a very strong nucleophile in pyridine, especially to the Si-atom of the linker.

  DOI：

  10.1002/1522-2675(200209)85:9<2930::aid-hlca2930>3.0.co;2-2

文献信息

• ——
  作者：Masatoshi Ushioda、Michinori Kadokura、Tomohisa Moriguchi、Akio Kobori、Morihiro Aoyagi、Kohji Seio、Mitsuo Sekine

  DOI：10.1002/1522-2675(200209)85:9<2930::aid-hlca2930>3.0.co;2-2

  日期：2002.9

  In connection with the synthesis of guanosine-capped of oligodeoxynucleotides on polymer supports, we found an unprecedented Si-O bond cleavage reaction, which occurred when polymer-linked oligodeoxynucleoticles having unprotected internucleotidic phosphate groups were allowed to react with the guanosine 5'-phosphorimidazolide derivative 18 in the presence of 4-nitro-6-(trifluoromethyl)-1H-benzotriazol-1-ol (Ntbt-OH) as an effective activator in pyridine. This side reaction was confirmed by the fact that the liquid-phase reaction of DMTrTpT-O-Si(iPr(2))OEt 42 with a simpler model compound. methyl phosphorimidazolide 34. in the presence of Ntbt-OH gave DMTrTpT 43. It turned out that the side reaction hardly occurs without unprotected internucleotidic phosphate groups on oligodeoxyriucleotides. The detailed study of this side reaction disclosed that Ntbt-OH directly attacks the Si-atom to release oligonucleotides from the resin. It is likely that Ntbt-OH serves as a very strong nucleophile in pyridine, especially to the Si-atom of the linker.