3'-O-[ethoxy(diisopropyl)silyl]-5'-O-[(9H-fluoren-9-ylmethoxy)carbonyl]thymidine | 497070-13-0

• 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-[ethoxy(diisopropyl)silyl]-5'-O-[(9H-fluoren-9-ylmethoxy)carbonyl]thymidine
• 英文别名: [(2R,3S,5R)-3-[ethoxy-di(propan-2-yl)silyl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl 9H-fluoren-9-ylmethyl carbonate
• CAS: 497070-13-0
• 化学式: C₃₃H₄₂N₂O₈Si
• 分子量: 622.791
• InChiKey: UIHNVJOXPVBVJW-FRXPANAUSA-N

物化性质

• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.78
• 重原子数：
  44
• 可旋转键数：
  13
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  113
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3'-O-[ethoxy(diisopropyl)silyl]-5'-O-[(9H-fluoren-9-ylmethoxy)carbonyl]thymidine 在 咪唑 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 生成 Carbonic acid (2R,3S,5R)-3-(chloro-diisopropyl-silanyloxy)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester 9H-fluoren-9-ylmethyl ester
  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：

  乙醇 、 Carbonic acid (2R,3S,5R)-3-(chloro-diisopropyl-silanyloxy)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester 9H-fluoren-9-ylmethyl ester 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以319 mg的产率得到3'-O-[ethoxy(diisopropyl)silyl]-5'-O-[(9H-fluoren-9-ylmethoxy)carbonyl]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