[(2R,3R,4R,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-2-(2,4-dioxopyrimidin-1-yl)-4-hydroxyoxolan-3-yl] N-methylcarbamate | 401916-32-3

• 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: [(2R,3R,4R,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-2-(2,4-dioxopyrimidin-1-yl)-4-hydroxyoxolan-3-yl] N-methylcarbamate
• CAS: 401916-32-3
• 化学式: C₃₂H₃₃N₃O₉
• 分子量: 603.629
• InChiKey: QNPQGVWRFDUFMC-YXINZVNLSA-N

物化性质

• 密度：
  1.39±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  44
• 可旋转键数：
  11
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  145
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  双(二异丙基氨基)(2-氰基乙氧基)膦 、 [(2R,3R,4R,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-2-(2,4-dioxopyrimidin-1-yl)-4-hydroxyoxolan-3-yl] N-methylcarbamate 在 四氮唑 、 二异丙胺 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 生成 [(2R,3R,4R,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-[2-cyanoethoxy-[di(propan-2-yl)amino]phosphanyl]oxy-2-(2,4-dioxopyrimidin-1-yl)oxolan-3-yl] N-methylcarbamate
  参考文献：
  名称：

  2′- O -Carbamate-containing oligonucleotides: synthesis and properties

  摘要：

  In order to evaluate the effect of a new T-carbohydrate modification on the hybridization properties of oligonucleotides, uridine 2-O-carbamates were synthesized and incorporated into DNA strands. The key intermediate in the synthesis, a mixed succinimide carbonate 2, was treated with various amines to give 2-O-carbamates 3. Thermal melting studies of modified oligonucleotides revealed that the presence of the 2-O-carbamate modification significantly destabilized DNA/RNA duplexes. A molecular-modeling study indicated that unfavorable steric interactions between the hydrogen of the NH group from the carbamate substituent and the anomeric hydrogen of the sugar residue on the same strand of the duplex may be the contributing factor causing destabilization. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)01908-6
• 作为产物：
  描述：

  [(2R,3R,4R,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-[tert-butyl(dimethyl)silyl]oxy-2-(2,4-dioxopyrimidin-1-yl)oxolan-3-yl] (2,5-dioxopyrrolidin-1-yl) carbonate 在 四丁基氟化铵 、 三乙胺 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 1.5h， 生成 [(2R,3R,4R,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-2-(2,4-dioxopyrimidin-1-yl)-4-hydroxyoxolan-3-yl] N-methylcarbamate
  参考文献：
  名称：

  2′- O -Carbamate-containing oligonucleotides: synthesis and properties

  摘要：

  In order to evaluate the effect of a new T-carbohydrate modification on the hybridization properties of oligonucleotides, uridine 2-O-carbamates were synthesized and incorporated into DNA strands. The key intermediate in the synthesis, a mixed succinimide carbonate 2, was treated with various amines to give 2-O-carbamates 3. Thermal melting studies of modified oligonucleotides revealed that the presence of the 2-O-carbamate modification significantly destabilized DNA/RNA duplexes. A molecular-modeling study indicated that unfavorable steric interactions between the hydrogen of the NH group from the carbamate substituent and the anomeric hydrogen of the sugar residue on the same strand of the duplex may be the contributing factor causing destabilization. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)01908-6