O⁶-cyanoethyl-N²-phenoxyacetyl-5′-O-(4,4′-dimethoxytrityl)-2′-O-(2-cyanoethoxymethyl)guanosine | 1333502-04-7

• 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: O⁶-cyanoethyl-N²-phenoxyacetyl-5′-O-(4,4′-dimethoxytrityl)-2′-O-(2-cyanoethoxymethyl)guanosine
• 英文别名: 5′-O-DMTr-2′-O-CEM-O⁶-cyanoethyl-N²-phenoxyacetylguanosine；N-[9-[(2R,3R,4R,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-3-(2-cyanoethoxymethoxy)-4-hydroxyoxolan-2-yl]-6-(2-cyanoethoxy)purin-2-yl]-2-phenoxyacetamide
• CAS: 1333502-04-7
• 化学式: C₄₆H₄₅N₇O₁₀
• 分子量: 855.904
• InChiKey: YYMDLYGSOYUMMQ-VOTRSWTQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  63
• 可旋转键数：
  21
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  214
• 氢给体数：
  2
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  (4R,5S)-oxazaphospholidine 、 O⁶-cyanoethyl-N²-phenoxyacetyl-5′-O-(4,4′-dimethoxytrityl)-2′-O-(2-cyanoethoxymethyl)guanosine 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 以54%的产率得到N-[9-[(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]-6-(2-cyanoethoxy)purin-2-yl]-2-phenoxyacetamide
  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：

  N²-phenoxyacetyl-3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)-2'-O-(2-cyanoethoxymethyl)guanosine 在 1-甲基吡咯烷 、 吡啶 、 4-二甲氨基吡啶 、 triethylamine tris(hydrogen fluoride) 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 12.59h， 生成 O⁶-cyanoethyl-N²-phenoxyacetyl-5′-O-(4,4′-dimethoxytrityl)-2′-O-(2-cyanoethoxymethyl)guanosine
  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.