5'-O-(4,4'-dimethoxytrityl)-N⁴-isobutyryl-2'-O-methylcytidine-3'-(methyl-N,N-diisopropylphosphonamidite) | 153809-40-6

• 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: 5'-O-(4,4'-dimethoxytrityl)-N⁴-isobutyryl-2'-O-methylcytidine-3'-(methyl-N,N-diisopropylphosphonamidite)
• 英文别名: N-[1-[(2R,3R,4R,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-[[di(propan-2-yl)amino]-methylphosphanyl]oxy-3-methoxyoxolan-2-yl]-2-oxopyrimidin-4-yl]-2-methylpropanamide
• CAS: 153809-40-6；153809-41-7；168752-56-5
• 化学式: C₄₂H₅₅N₄O₈P
• 分子量: 774.894
• InChiKey: ZWZQOFGHEWDFET-CMUCOHJHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  55
• 可旋转键数：
  17
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  120
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  5'-O-(4,4'-dimethoxytrityl)-N⁴-isobutyryl-2'-O-methylcytidine-3'-(methyl-N,N-diisopropylphosphonamidite) 在 吡啶 、 四氮唑 、 3-ethyl-3-pentanoxymagnesium chloride 、 四丁基氟化铵 、 碘 作用下， 反应 2.38h， 生成
  参考文献：
  名称：

  Diastereoselective Synthesis of 2′-Deoxy and 2′-O-Methyl Dinucleoside (3′ 5′)-Methylphosphonates via Alkoxymagnesium Chloride-Mediated Nucleoside Coupling

  摘要：

  A diastereoselective dinucleoside methylphosphonate synthetic method that features coupling of diastereomerically pure 1,1,1,3,3,3-hexafluoro-2-propyl nucleoside-3'-O-methylphosphonate monomers with 3'-O-protected nucleoside monomers mediated by alkoxymagnesium chloride reagents is described. This synthetic method was found to be diastereospecific in the synthesis of selected 2'-deoxy dinucleoside methyphosphonates and diastereoselective in the synthesis of all sixteen 2'-O-methyl dinucleoside methylphosphonates.

  DOI：

  10.1080/07328319708001359
• 作为产物：
  描述：

  胞苷 在 吡啶 、 水 、 triethylamine tris(hydrogen fluoride) 、 三乙胺 、 N,N-二异丙基乙胺 、 silver(l) oxide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 苯 为溶剂， 反应 8.5h， 生成 5'-O-(4,4'-dimethoxytrityl)-N⁴-isobutyryl-2'-O-methylcytidine-3'-(methyl-N,N-diisopropylphosphonamidite)
  参考文献：
  名称：

  A Convenient High Yield Synthesis of N⁴-Isobutyryl-2′-O-Methylcytidine and Its Monomer Units For Incorporation into Oligonucleotides

  摘要：

  We designed an efficient three step procedure for the synthesis of N-4-isobutyryl-2'-O-methylcytidine. This protected nucleoside was then used to prepare a methylphosphonamidite monomer for incorporation into oligonucleotides. Transamination at the C-4 position of cytidine using ethylenediamine, which has been reported for the N-4-benzoyl cytidine, was not observed with N-4-isobutyryl protected 2'-O-methylcytidine

  DOI：

  10.1080/07328319308016200

文献信息

• A Convenient High Yield Synthesis of N⁴-Isobutyryl-2′-O-Methylcytidine and Its Monomer Units For Incorporation into Oligonucleotides
  作者：Morteza M. Vaghefi、Richard I. Hogrefe

  DOI：10.1080/07328319308016200

  日期：1993.12

  We designed an efficient three step procedure for the synthesis of N-4-isobutyryl-2'-O-methylcytidine. This protected nucleoside was then used to prepare a methylphosphonamidite monomer for incorporation into oligonucleotides. Transamination at the C-4 position of cytidine using ethylenediamine, which has been reported for the N-4-benzoyl cytidine, was not observed with N-4-isobutyryl protected 2'-O-methylcytidine
• Diastereoselective Synthesis of 2′-Deoxy and 2′-O-Methyl Dinucleoside (3′ 5′)-Methylphosphonates via Alkoxymagnesium Chloride-Mediated Nucleoside Coupling
  作者：William J. Daily、David A. Schwartz、Timothy A. Riley、Lyle J. Arnold、William B. Marvin、Michael A. Scurria、Stephanie A. Hopkins、Michael B. Atkins、Christine D. Garcia、Michael C. Pirrung

  DOI：10.1080/07328319708001359

  日期：1997.4

  A diastereoselective dinucleoside methylphosphonate synthetic method that features coupling of diastereomerically pure 1,1,1,3,3,3-hexafluoro-2-propyl nucleoside-3'-O-methylphosphonate monomers with 3'-O-protected nucleoside monomers mediated by alkoxymagnesium chloride reagents is described. This synthetic method was found to be diastereospecific in the synthesis of selected 2'-deoxy dinucleoside methyphosphonates and diastereoselective in the synthesis of all sixteen 2'-O-methyl dinucleoside methylphosphonates.