(Sp)-5'-O-(4,4'-dimethoxytrityl)-2'-deoxythymidylyl-(3'->5')-3'-O-[(1,1-dimethylethyl)diphenylsilyl]-2'-deoxythymidine 3'-methylphosphonate | 195307-35-8

• 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: (Sp)-5'-O-(4,4'-dimethoxytrityl)-2'-deoxythymidylyl-(3'->5')-3'-O-[(1,1-dimethylethyl)diphenylsilyl]-2'-deoxythymidine 3'-methylphosphonate
• 英文别名: 1-[(2R,4S,5R)-5-[[[(2R,3S,5R)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]oxy-methylphosphoryl]oxymethyl]-4-[tert-butyl(diphenyl)silyl]oxyoxolan-2-yl]-5-methylpyrimidine-2,4-dione
• CAS: 195307-35-8
• 化学式: C₅₈H₆₅N₄O₁₃PSi
• 分子量: 1085.23
• InChiKey: LRPNFMQCFCVIMK-NQOQOWAKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.47
• 重原子数：
  77.0
• 可旋转键数：
  19.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  200.63
• 氢给体数：
  2.0
• 氢受体数：
  15.0

反应信息

• 作为反应物：
  描述：

  (Sp)-5'-O-(4,4'-dimethoxytrityl)-2'-deoxythymidylyl-(3'->5')-3'-O-[(1,1-dimethylethyl)diphenylsilyl]-2'-deoxythymidine 3'-methylphosphonate 在 四丁基氟化铵 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.5h， 生成 5'-O-(4,4'-dimethoxytrityl)-2'-deoxythymidylyl-(3'->5')-3'-O-[(2-cyanoethyl)-N,N-diisopropylamido-phosphoramidite]-2'-deoxythymidine 3'-(Sp)-methylphosphonate
  参考文献：
  名称：

  Schweitzer, Markus; Engels, Joachim W., Nucleosides and Nucleotides, 1998, vol. 17, # 1-3, p. 317 - 326

  摘要：

  DOI：
• 作为产物：
  描述：

  5'-dimethoxytritylthymidine-3'-diisopropylaminomethylphosphonoamidite 在 叔丁基过氧化氢 、 2-(triphenylmethyl)-4,5-dicyanoimidazole 作用下， 以 二氯甲烷 为溶剂， 生成 (Sp)-5'-O-(4,4'-dimethoxytrityl)-2'-deoxythymidylyl-(3'->5')-3'-O-[(1,1-dimethylethyl)diphenylsilyl]-2'-deoxythymidine 3'-methylphosphonate
  参考文献：
  名称：

  Triarylmethyl Substituted 4,5-Dicyanoimidazoles as Activators for Rp-Diastereoselective Synthesis of TpN Dinucleoside Methylphosphonates

  摘要：

  2-Triarylmethyl-4,5-dicyanoimidazoles 1-3 were synthesized and tested as activators in the methylphosphonamidite approach. TpN dinucleoside methylphosphonates generated showed diastereoselectivity of up to 8 / 1 (Rp / Sp). The influence of the different triarylmethyl substituents on diastereoselectivity is shown.

  DOI：

  10.1080/07328319908044654

文献信息

• 5-[2-(2-Methoxy)bornyl]tetrazole as Catalyst for Diastereoselective Synthesis of 2′-Deoxy Dinucleoside (3′, 5′)-Methylphosphonates
  作者：Peter Schell、Joachim W. Engels

  DOI：10.1080/07328319708002948

  日期：1997.5

  The synthesis of 5-[2-(2-methoxy)bornyl]tetrazore 1 is described. 1 is used as catalyst for the diastereoselective synthesis of some 2'-deoxy dinucleoside (3',5')-methylphosphonates in solution.
• Rp-Diastereoselective synthesis of dinucleoside methylphosphonates by the phosphoramidite approach
  作者：Peter Schell、Joachim W. Engels

  DOI：10.1016/s0040-4039(98)01972-8

  日期：1998.11

  In order to obtain diastereomeric control in the azole catalyzed coupling reaction of methylphosphonamidites, 2-(2',4',6'-trimethylbiphenyl-2-yl)-4,5-dicyanoimidazole 2 was synthesized. With its use as activator Rp-diastereoselective synthesis of dinucleoside methylphosphonates could be achieved for the first time by the phosphoramidite approach. Selectivities were up to 84 / 16 (Rp / Sp). The mechanism of the reaction is based on dynamic kinetic resolution. (C) 1998 Elsevier Science Ltd. All rights reserved.