1,3-dimethyl-5'-O-(4,4'-dimethoxytrityl)-2'-deoxy-ψ-uridine | 162604-83-3

• 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: 1,3-dimethyl-5'-O-(4,4'-dimethoxytrityl)-2'-deoxy-ψ-uridine
• CAS: 162604-83-3
• 化学式: C₃₂H₃₄N₂O₇
• 分子量: 558.631
• InChiKey: BEBZXKNVIVGFCS-ZGIBFIJWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  41.0
• 可旋转键数：
  9.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  101.15
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  1,3-dimethyl-5'-O-(4,4'-dimethoxytrityl)-2'-deoxy-ψ-uridine 在 N,N-二异丙基乙胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 16.75h， 生成 2-N-methyl-5'-O-(4,4'-dimethoxytrityl)-2'-deoxy-α-ψ-isocytidine-3'-<2-cyanoethyl bis(1-methylethyl)>phosphoramidite
  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：

  (1R)-1,4-脱水-2-脱氧-1-(1,3-二甲基-2,4-二氧代-1,2,3,4-四氢-5-嘧啶基)-D-赤式-戊糖醇 、 4,4'-双甲氧基三苯甲基氯 以 吡啶 为溶剂， 反应 2.0h， 以75%的产率得到1,3-dimethyl-5'-O-(4,4'-dimethoxytrityl)-2'-deoxy-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