N1-methyl-2'-O-allyl-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-ψ-uridine | 162604-94-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: N1-methyl-2'-O-allyl-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-ψ-uridine
• CAS: 162604-94-6
• 化学式: C₂₅H₄₄N₂O₇Si₂
• 分子量: 540.805
• InChiKey: HDFAWIMOAXXMBW-ACESQOTJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.04
• 重原子数：
  36.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  101.01
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  N1-methyl-2'-O-allyl-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-ψ-uridine 在 四丁基氟化铵 、 三乙胺 作用下， 以 四氢呋喃 、 吡啶 为溶剂， 反应 2.5h， 生成 N1-methyl-2'-O-allyl-5'-O-(4,4'-dimethoxytrityl)-ψ-uridine
  参考文献：
  名称：

  A Facile Synthesis of the Phosphoramidites of 2-N-Methyl-2′-deoxy (or 2′-O-allyl)-ψ-isocytidine, 1, 3-Dimethyl-2′-deoxy-ψ-uridine andN1-Methyl-2′-O-allyl-ψ-uridine as Synthons Suitable for Oligonucleotide Synthesis

  摘要：

  An efficient and facile syntheses of 5'-O-(4,4'-dimethoxytrityl)-3'-[2-cyanoethyl bis(1-methylethyl)]phosphoramidites of 2-N-methyl-2'-deoxy-psi-isocytidine (h), 2-N-methyl-2'-deoxy-alpha-psi-isocytidine (13 ), 2-N-methyl-2'-O-allyl-psi-isocytidine (11), 1,3-dimethyl-2'-deoxy-psi-uridine (4) and N1-methyl-2'-O-allyl-psi-uridine (19) have been accomplished in good overall yields. The pyrimidine-pyrimidine transformation reaction was found to be useful for the preparation of 2-N-methyl-2'-O-allyl-psi-isocytidine (10). The utility of these novel phosphoramidites is demonstrated by their incorporation into oligonucleotides via solid-support, oligonucleotide methodology.

  DOI：

  10.1080/15257779408009476
• 作为产物：
  描述：

  1,3二氯-1,1,3,3-四异丙基二硅氧烷 在 tris-(dibenzylideneacetone)dipalladium(0) 、 1,4-双(二苯基膦)丁烷 作用下， 以 四氢呋喃 、 吡啶 为溶剂， 反应 9.0h， 生成 N1-methyl-2'-O-allyl-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-ψ-uridine
  参考文献：
  名称：

  A Facile Synthesis of the Phosphoramidites of 2-N-Methyl-2′-deoxy (or 2′-O-allyl)-ψ-isocytidine, 1, 3-Dimethyl-2′-deoxy-ψ-uridine andN1-Methyl-2′-O-allyl-ψ-uridine as Synthons Suitable for Oligonucleotide Synthesis

  摘要：

  An efficient and facile syntheses of 5'-O-(4,4'-dimethoxytrityl)-3'-[2-cyanoethyl bis(1-methylethyl)]phosphoramidites of 2-N-methyl-2'-deoxy-psi-isocytidine (h), 2-N-methyl-2'-deoxy-alpha-psi-isocytidine (13 ), 2-N-methyl-2'-O-allyl-psi-isocytidine (11), 1,3-dimethyl-2'-deoxy-psi-uridine (4) and N1-methyl-2'-O-allyl-psi-uridine (19) have been accomplished in good overall yields. The pyrimidine-pyrimidine transformation reaction was found to be useful for the preparation of 2-N-methyl-2'-O-allyl-psi-isocytidine (10). The utility of these novel phosphoramidites is demonstrated by their incorporation into oligonucleotides via solid-support, oligonucleotide methodology.

  DOI：

  10.1080/15257779408009476