N,N-diisopropylamino <2-(trimethylsilyl)ethyl>phosphorochloridite | 154664-89-8

• 分子结构分类: 有机化合物 - 有机盐 - 有机金属盐
• 英文名称: N,N-diisopropylamino <2-(trimethylsilyl)ethyl>phosphorochloridite
• 英文别名: N-[chloro(2-trimethylsilylethoxy)phosphanyl]-N-propan-2-ylpropan-2-amine
• CAS: 154664-89-8
• 化学式: C₁₁H₂₇ClNOPSi
• 分子量: 283.854
• InChiKey: PLZHORJQSBPGNB-UHFFFAOYSA-N

物化性质

• 沸点：
  289.4±42.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.93
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N,N-diisopropylamino <2-(trimethylsilyl)ethyl>phosphorochloridite 在 四氮唑 、 叔丁基过氧化氢 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成
  参考文献：
  名称：

  New Nucleoside−Sugar Conjugates:  6-N-Glycosyloxyphosphorylated Adenosine Derivatives as Partial Structures of Agrocin 84

  摘要：

  We report the first successful synthesis of 6-N-[(glucofuranos-1-yloxy)phosphoryl]adenosine as a partial structure of Agrocin 84 via a two-step phosphorylation of 2',3',5'-tri-O-benzoyladenosine with a 2,3,5,6-tetra-O-acetylglucofuranoside 1-O-phosphoramidite derivative that has a 2-(trimethylsilyl)ethyl group as the phosphate protecting group. A similar nucleoside-sugar conjugate, 6-N-[(ribofuranos-1-yloxy)phosphoryl]ade was also synthesized. The stabilities of these 6-N-[(glycos-1-yloxy)phosphoryl] adeno sine derivatives under acidic, basic, and thermal conditions are described. In particular, we found that the P-O bond of these sugar-nucleoside conjugates was selectively cleaved by treatment with 0.1 M NaOH to give 6-N-phosphoryladenosine, while acidic treatment gave directly adenosine with cleavage of the P-N bond.

  DOI：

  10.1021/jo961489a
• 作为产物：
  描述：

  trimethyl(2-(trimethylsilyl)ethoxy)silane 在 三氯化磷 作用下， 以 乙醚 为溶剂， 反应 1.0h， 生成 N,N-diisopropylamino <2-(trimethylsilyl)ethyl>phosphorochloridite
  参考文献：
  名称：

  2-（三甲基甲硅烷基）乙基为寡核苷酸合成中的磷酸酯保护基

  摘要：

  发现2-（三甲基甲硅烷基）乙基（TSE）基团作为寡核苷酸合成中核苷酸间磷酸的保护基是有效的。具有良好产率的具有TSE基团的亚磷酰胺构件被制备。在脱氧鸟苷的情况下，合成了2- N-未保护的亚磷酰胺结构单元。这些化合物被用于寡脱氧核糖核苷酸的固相合成。通过31 P NMR阐明了与未保护的鸟嘌呤部分相关的副反应。

  DOI：

  10.1016/s0040-4039(00)75810-2

文献信息

• 2-(trimethylsilyl)ethyl as a phosphate protecting group in oligonucleotide synthesis
  作者：Takeshi Wada、Mitsuo Sekine

  DOI：10.1016/s0040-4039(00)75810-2

  日期：1994.1

  The 2-(trimethylsilyl)ethyl (TSE) group was found to be effective as a protecting group for the internucleotidic phosphate in oligonucleotide synthesis. Phosphoramidite building blocks having the TSE group were prepared in good yields. In the case of deoxyguanosine, a 2-N-unprotected phosphoramidite building block was synthesized. These compounds were applied to the solid-phase synthesis of oligodeoxyribonucleotides

  发现2-（三甲基甲硅烷基）乙基（TSE）基团作为寡核苷酸合成中核苷酸间磷酸的保护基是有效的。具有良好产率的具有TSE基团的亚磷酰胺构件被制备。在脱氧鸟苷的情况下，合成了2- N-未保护的亚磷酰胺结构单元。这些化合物被用于寡脱氧核糖核苷酸的固相合成。通过31 P NMR阐明了与未保护的鸟嘌呤部分相关的副反应。
• New Nucleoside−Sugar Conjugates:  6-<i>N</i>-Glycosyloxyphosphorylated Adenosine Derivatives as Partial Structures of Agrocin 84
  作者：Tomohisa Moriguchi、Takeshi Wada、Mitsuo Sekine

  DOI：10.1021/jo961489a

  日期：1996.1.1

  We report the first successful synthesis of 6-N-[(glucofuranos-1-yloxy)phosphoryl]adenosine as a partial structure of Agrocin 84 via a two-step phosphorylation of 2',3',5'-tri-O-benzoyladenosine with a 2,3,5,6-tetra-O-acetylglucofuranoside 1-O-phosphoramidite derivative that has a 2-(trimethylsilyl)ethyl group as the phosphate protecting group. A similar nucleoside-sugar conjugate, 6-N-[(ribofuranos-1-yloxy)phosphoryl]ade was also synthesized. The stabilities of these 6-N-[(glycos-1-yloxy)phosphoryl] adeno sine derivatives under acidic, basic, and thermal conditions are described. In particular, we found that the P-O bond of these sugar-nucleoside conjugates was selectively cleaved by treatment with 0.1 M NaOH to give 6-N-phosphoryladenosine, while acidic treatment gave directly adenosine with cleavage of the P-N bond.