1-[(2R,3R,4R,5R)-4-[tert-butyl(diphenyl)silyl]oxy-3-methoxy-5-(methylaminooxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione | 198703-67-2

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 1-[(2R,3R,4R,5R)-4-[tert-butyl(diphenyl)silyl]oxy-3-methoxy-5-(methylaminooxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione
• CAS: 198703-67-2
• 化学式: C₂₈H₃₇N₃O₆Si
• 分子量: 539.704
• InChiKey: LJJSEDHHMKEWJT-PMHJDTQVSA-N

物化性质

• 密度：
  1.21±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.85
• 重原子数：
  38
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  98.4
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-[(2R,3R,4R,5R)-4-[tert-butyl(diphenyl)silyl]oxy-3-methoxy-5-(methylaminooxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione 在 吡啶硼烷 、 4-甲基苯磺酸吡啶 、 triethylamine tris(hydrogen fluoride) 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成
  参考文献：
  名称：

  The Synthesis of the Sixteen Possible 2′-O-Methyl MMI Dimer Phosphoramidites: Building Blocks for the Synthesis of Novel Antisense Oligonucleotides

  摘要：

  DOI：

  10.1080/07328319708006118
• 作为产物：
  描述：

  5'-O-amino-3'-O-tert-butyldiphenylsilyl-2'-O-methyl-5-methyluridine 在 sodium cyanoborohydride 作用下， 以 甲醇 、 溶剂黄146 、 乙酸乙酯 为溶剂， 反应 2.5h， 生成 1-[(2R,3R,4R,5R)-4-[tert-butyl(diphenyl)silyl]oxy-3-methoxy-5-(methylaminooxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione
  参考文献：
  名称：

  An Efficient Multigram Synthesis of Monomers for the Preparation of Novel Oligonucleotides Containing Isosteric Non-Phosphorous Backbones

  摘要：

  The facile preparation of two novel classes of nucleoside analogs for the inclusion as dimeric non-phosphorous containing subunits in chimeric backbones has been accomplished. The concise preparation of 3'-formylnucleosides and 5'-O-(N-methylhydroxylamino)-nucleosides is reported.

  DOI：

  10.1080/07328319708006242

文献信息

• A new approach for the synthesis of 3′-deoxy-3′-C-formyl-ribonucleosides and the synthesis of alternating methylene(methylimino) linked phosphodiester backbone oligonucleotides with 2′-OH and 2′-OMe groups
  作者：Marija Prhavc、George Just*、Balkrishen Bhat、P.Dan Cook、Muthiah Manoharan

  DOI：10.1016/s0040-4039(00)01814-1

  日期：2000.12

  A stereoselective synthesis of 3'-deoxy-3'-C-formyl-5-methyluridine 2 is described via the dithiane 4 as the key intermediate. Compound 2 was coupled with 3 into a novel ribo-MMI dimer 1. The dimer was then incorporated into antisense oligonucleotides which were found to have high binding affinity to the target RNA. (C) 2000 Elsevier Science Ltd. All rights reserved.