N'-[9-((3aR,4R,6R,6aR)-2-Dimethylamino-6-hydroxymethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-9H-purin-6-yl]-N,N-dimethyl-formamidine | 17331-18-9

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: N'-[9-((3aR,4R,6R,6aR)-2-Dimethylamino-6-hydroxymethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-9H-purin-6-yl]-N,N-dimethyl-formamidine
• 英文别名: N'-[9-[(3aR,4R,6R,6aR)-2-(dimethylamino)-6-(hydroxymethyl)-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]purin-6-yl]-N,N-dimethylmethanimidamide
• CAS: 17331-18-9
• 化学式: C₁₆H₂₃N₇O₄
• 分子量: 377.403
• InChiKey: ZBSXUQHNUBVFFW-IVZLEWBYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  110
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  N'-[9-((3aR,4R,6R,6aR)-2-Dimethylamino-6-hydroxymethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-9H-purin-6-yl]-N,N-dimethyl-formamidine 在 甲醇 作用下， 以 吡啶 为溶剂， 反应 4.0h， 生成 5'-O-(4,4'-dimethoxytrityl)-N⁶-dimethylaminomethyleneadenosine
  参考文献：
  名称：

  High yield protection of purine ribonucleosides for H-phosphonate RNA synthesis

  摘要：

  We report a new method for protecting nucleosides for hydrogen phosphonate RNA synthesis that gives very high yields for the purines. This method is based on our finding that, for adenosine and guanosine, silylation of a mixture of 2' and 3' H-phosphonates in the presence of DBU is highly selective for the 2' hydroxyl. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)01767-x
• 作为产物：
  描述：

  N,N-二甲基甲酰胺二甲基缩醛 、 腺苷 以 吡啶 为溶剂， 反应 15.0h， 生成 N'-[9-((3aR,4R,6R,6aR)-2-Dimethylamino-6-hydroxymethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-9H-purin-6-yl]-N,N-dimethyl-formamidine
  参考文献：
  名称：

  High yield protection of purine ribonucleosides for H-phosphonate RNA synthesis

  摘要：

  We report a new method for protecting nucleosides for hydrogen phosphonate RNA synthesis that gives very high yields for the purines. This method is based on our finding that, for adenosine and guanosine, silylation of a mixture of 2' and 3' H-phosphonates in the presence of DBU is highly selective for the 2' hydroxyl. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)01767-x

文献信息

• High yield protection of purine ribonucleosides for H-phosphonate RNA synthesis
  作者：Xiaohu Zhang、José-Luis Abad、Qingtao Huang、Fan Zeng、Barbara L. Gaffney、Roger A. Jones

  DOI：10.1016/s0040-4039(97)01767-x

  日期：1997.10

  We report a new method for protecting nucleosides for hydrogen phosphonate RNA synthesis that gives very high yields for the purines. This method is based on our finding that, for adenosine and guanosine, silylation of a mixture of 2' and 3' H-phosphonates in the presence of DBU is highly selective for the 2' hydroxyl. (C) 1997 Elsevier Science Ltd.
• High yield protection of purine ribonucleosides for phosphoramidite RNA synthesis
  作者：Quanlai Song、Weimin Wang、Artur Fischer、Xiaohu Zhang、Barbara L. Gaffney、Roger A. Jones

  DOI：10.1016/s0040-4039(99)00733-9

  日期：1999.5

  We report high yield procedures for protection of purine ribonucleosides based on a reaction which allows concomitant highly regiospecific 2'-silylation and 3'-phosphitylation. Subsequent cleavage of the H-phosphonate monoester moiety without silyl migration provides intermediates ready for phosphitylation by standard methods to give fully protected phosphoramidites. (C) 1999 Elsevier Science Ltd. All rights reserved.