N-[1-[(2R,3R,4R,5R)-4-[[(1S,3S,3aR)-3-phenyl-3a,4,5,6-tetrahydro-3H-pyrrolo[1,2-c][1,3,2]oxazaphosphol-1-yl]oxy]-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-3-(2-cyanoethoxymethoxy)oxolan-2-yl]-2-oxopyrimidin-4-yl]acetamide | 1333502-11-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: N-[1-[(2R,3R,4R,5R)-4-[[(1S,3S,3aR)-3-phenyl-3a,4,5,6-tetrahydro-3H-pyrrolo[1,2-c][1,3,2]oxazaphosphol-1-yl]oxy]-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-3-(2-cyanoethoxymethoxy)oxolan-2-yl]-2-oxopyrimidin-4-yl]acetamide
• CAS: 1333502-11-6
• 化学式: C₄₇H₅₀N₅O₁₀P
• 分子量: 875.915
• InChiKey: AZCCQOYVKDVABS-YOMXZTRMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  63
• 可旋转键数：
  18
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  163
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  N-[1-[(2R,3R,4R,5R)-4-[[(1S,3S,3aR)-3-phenyl-3a,4,5,6-tetrahydro-3H-pyrrolo[1,2-c][1,3,2]oxazaphosphol-1-yl]oxy]-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-3-(2-cyanoethoxymethoxy)oxolan-2-yl]-2-oxopyrimidin-4-yl]acetamide 、 alkaline earth salt of/the/ methylsulfuric acid 在 N-氰甲基吡咯烷鎓三氟甲烷磺酸盐 、 N,N'-dimethylthioperoxydicarbamic acid 作用下， 以 乙腈 为溶剂， 反应 0.25h， 以95%的产率得到
  参考文献：
  名称：

  Stereocontrolled Solid-Phase Synthesis of Phosphorothioate Oligoribonucleotides Using 2′-O-(2-Cyanoethoxymethyl)-nucleoside 3′-O-Oxazaphospholidine Monomers

  摘要：

  A method for the synthesis of P-stereodefined phosphorothioate oligoribonucleotides (PS-ORNs) was developed. PS-ORNs of mixed sequence (up to 12mers) were successfully synthesized by this method with sufficient coupling efficiency (94-99%) and diastereoselectivity (>= 98:2). The coupling efficiency was greatly improved by the use of 2-cyanoethoxymethyl (CEM) groups in place of the conventional TBS groups for the 2'-O-protection of nucleoside 3'-O-oxazaphospholidine monomers. The resultant diastereopure PS-ORNs allowed us to clearly demonstrate that an ORN containing an all-(Rp)-PS-backbone stabilizes its duplex with the complementary ORN, whereas its all-(Sp)-counterpart has a destabilizing effect.

  DOI：

  10.1021/jo301052v
• 作为产物：
  描述：

  N⁴-acetyl-5′-O-(4,4′-dimethoxytrityl)-2′-O-(2-cyanoethoxymethyl)cytidine 、 (4R,5S)-oxazaphospholidine 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 以75%的产率得到N-[1-[(2R,3R,4R,5R)-4-[[(1S,3S,3aR)-3-phenyl-3a,4,5,6-tetrahydro-3H-pyrrolo[1,2-c][1,3,2]oxazaphosphol-1-yl]oxy]-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-3-(2-cyanoethoxymethoxy)oxolan-2-yl]-2-oxopyrimidin-4-yl]acetamide
  参考文献：
  名称：

  Stereocontrolled Solid-Phase Synthesis of Phosphorothioate Oligoribonucleotides Using 2′-O-(2-Cyanoethoxymethyl)-nucleoside 3′-O-Oxazaphospholidine Monomers

  摘要：

  A method for the synthesis of P-stereodefined phosphorothioate oligoribonucleotides (PS-ORNs) was developed. PS-ORNs of mixed sequence (up to 12mers) were successfully synthesized by this method with sufficient coupling efficiency (94-99%) and diastereoselectivity (>= 98:2). The coupling efficiency was greatly improved by the use of 2-cyanoethoxymethyl (CEM) groups in place of the conventional TBS groups for the 2'-O-protection of nucleoside 3'-O-oxazaphospholidine monomers. The resultant diastereopure PS-ORNs allowed us to clearly demonstrate that an ORN containing an all-(Rp)-PS-backbone stabilizes its duplex with the complementary ORN, whereas its all-(Sp)-counterpart has a destabilizing effect.

  DOI：

  10.1021/jo301052v

文献信息

• Stereocontrolled Solid-Phase Synthesis of Phosphorothioate Oligoribonucleotides Using 2′-<i>O</i>-(2-Cyanoethoxymethyl)-nucleoside 3′-<i>O</i>-Oxazaphospholidine Monomers
  作者：Yohei Nukaga、Kohei Yamada、Toshihiko Ogata、Natsuhisa Oka、Takeshi Wada

  DOI：10.1021/jo301052v

  日期：2012.9.21

  A method for the synthesis of P-stereodefined phosphorothioate oligoribonucleotides (PS-ORNs) was developed. PS-ORNs of mixed sequence (up to 12mers) were successfully synthesized by this method with sufficient coupling efficiency (94-99%) and diastereoselectivity (>= 98:2). The coupling efficiency was greatly improved by the use of 2-cyanoethoxymethyl (CEM) groups in place of the conventional TBS groups for the 2'-O-protection of nucleoside 3'-O-oxazaphospholidine monomers. The resultant diastereopure PS-ORNs allowed us to clearly demonstrate that an ORN containing an all-(Rp)-PS-backbone stabilizes its duplex with the complementary ORN, whereas its all-(Sp)-counterpart has a destabilizing effect.