[9-[(2R,4S,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-hydroxyoxolan-2-yl]-2-(propanoylamino)purin-6-yl] N,N-diphenylcarbamate | 87036-65-5

• 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: [9-[(2R,4S,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-hydroxyoxolan-2-yl]-2-(propanoylamino)purin-6-yl] N,N-diphenylcarbamate
• CAS: 87036-65-5
• 化学式: C₄₇H₄₄N₆O₈
• 分子量: 820.902
• InChiKey: FABFQXHEQBYXNO-USBBMYKGSA-N

物化性质

• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  61
• 可旋转键数：
  15
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  159
• 氢给体数：
  2
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  [9-[(2R,4S,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-hydroxyoxolan-2-yl]-2-(propanoylamino)purin-6-yl] N,N-diphenylcarbamate 在 吡啶 作用下， 以 吡啶 为溶剂， 反应 8.25h， 生成 Diphenyl-carbamic acid 9-[(2R,4S,5R)-5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-(hydroxy-phenylsulfanyl-phosphoryloxy)-tetrahydro-furan-2-yl]-2-propionylamino-9H-purin-6-yl ester; compound with triethyl-amine
  参考文献：
  名称：

  Diphenylcarbamoyl and propionyl groups: a new combination of protecting groups for the guanine residue

  摘要：

  DOI：

  10.1016/s0040-4039(00)88019-3
• 作为产物：
  描述：

  2'-脱氧鸟苷 在 吡啶 、 4-二甲氨基吡啶 、 sodium hydroxide 、 N,N-二异丙基乙胺 作用下， 以 吡啶 、 乙醇 为溶剂， 反应 2.42h， 生成 [9-[(2R,4S,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-hydroxyoxolan-2-yl]-2-(propanoylamino)purin-6-yl] N,N-diphenylcarbamate
  参考文献：
  名称：

  Diphenylcarbamoyl and propionyl groups: a new combination of protecting groups for the guanine residue

  摘要：

  DOI：

  10.1016/s0040-4039(00)88019-3

文献信息

• Nucleoside 3′-N,N-Dialkylphosphonamidates as novel nucleotide units for the solution-phase oligonucleotide synthesis
  作者：Takeshi Wada、Kazushige Ishikawa、Tsujiaki Hata

  DOI：10.1016/s0040-4020(01)86304-3

  日期：1993.3

  3′-N,N,-diisopropylphosphonamidate building blocks for oligonucleotide synthesis were prepared in high yields from appropriately protected nucleosides by use of chlorobis(N,N,-diisopropylamino)phosphine as a phosphitylating reagent. The 5′-dimethoxytrityl group of the nucleoside 3′-N,N-diisopropylphosphonamidates was removed selectively without cleavage of the P-N bond under mild acidic conditions

  通过使用氯代双（N，N，-二异丙基氨基）膦作为磷酸化试剂，由适当保护的核苷以高收率制备用于寡核苷酸合成的核苷3'-N，N，-二异丙基氨基膦酸酯结构单元。在温和的酸性条件下，可选择性除去核苷3'-N，N-N，N-二异丙基膦酰胺的5'-二甲氧基三苯甲基，而不会裂解PN键。发现核苷3'-N，N-二异丙基膦酰胺酸酯对叔丁基氢过氧化物的氧化具有抗性。尝试使用磷酸亚氨基酯结构单元向5'-和3'-方向延伸链，并合成了三胸苷酸。发现核苷3'-N，N，N-二异丙基膦酰胺可能用作溶液相寡核苷酸合成的3'-末端核苷酸单元。
• Synthesis of Oligodeoxyribonucleotides Involving a Rapid Procedure for Removal of Base-Protecting Groups by Use of the 4,4′,4″-Tris(benzoyloxy)trityl (TBTr) Group
  作者：Mitsuo Sekine、Narihiro Masuda、Tsujiaki Hata

  DOI：10.1246/bcsj.59.1781

  日期：1986.6

  protected building units for oligodeoxyribonucleotide synthesis in the phosphoramidite approach were prepared in high yields by the 5′-dimethoxytritylation of N-[4,4′,4″-tris(benzoyloxy)trityl]deoxyribonucleosides followed by the 3′-phosphitylation with methoxymorpholinochlorophosphine. The solid phase synthesis of oligodeoxyribonucleotides on a controlled pore glass gel using the amidite units was examined

  通过 N-[4,4',4"-三(苯甲酰氧基)三苯甲基]脱氧核糖核苷的 5'-二甲氧基三苯甲基化，然后用甲氧基吗啉代氯膦进行 3'-亚磷酸化，以高产率制备了用于亚磷酰胺方法中寡脱氧核糖核苷酸合成的完全保护的构建单元. 检查了使用亚酰胺单元在受控孔玻璃凝胶上的寡脱氧核糖核苷酸的固相合成。详细讨论了冷凝效率。4,4',4"-三（苯甲酰氧基）三苯甲基（TBTr）基团从受控孔玻璃凝胶上合成的受保护四聚体中快速去除，得到 dGpCpApT。
• Preparation and screening of highly diverse peptide libraries for binding activity
  申请人：INTERPHARM LABORATORIES LTD.

  公开号：EP0639584A1

  公开（公告）日：1995-02-22

  A method for the preparation of high density peptide (or other polymer) libraries, and for screening such libraries for molecules having the capacity to recognize targets of choice, is provided.

  本研究提供了一种制备高密度多肽（或其他聚合物）文库的方法，以及筛选此类文库中具有识别所选靶标能力的分子的方法。
• Nonoxidative chlorination of dialkyl phosphonates to dialkyl phosphorochloridites. A new approach to oligonucleotide synthesis
  作者：Takeshi Wada、Ryohei Kato、Tsujiaki Hata

  DOI：10.1021/jo00003a056

  日期：1991.2

  Several dialkyl phosphonates and alkyl nucleoside 3'-phosphonates were transformed into the corresponding highly reactive phosphorochloridites without oxidation of phosphorus by use of tris(2,4,6-tribromophenoxy)-dichlorophosphorane (BDCP) as a chlorinating reagent. The reaction was applied to internucleotidic bond formation. 2-Cyanoethyl and methyl nucleoside 3'-phosphonates were prepared in high yields and were stable enough to be used as starting materials in oligonucleotide synthesis. Examination of dodecathymidylate synthesis on a polymer support, using 2-cyanoethyl or methyl nucleoside 3'-phosphonate as building blocks, showed that the 2-cyanoethyl nucleoside 3'-phosphonate was more effective.
• Biologically Active Oligodeoxyribonucleotides. 5. 5‘-End-Substituted d(TGGGAG) Possesses Anti-Human Immunodeficiency Virus Type 1 Activity by Forming a G-Quadruplex Structure
  作者：Hitoshi Hotoda、Makoto Koizumi、Rika Koga、Masakatsu Kaneko、Kenji Momota、Toshinori Ohmine、Hidehiko Furukawa、Toshinori Agatsuma、Takashi Nishigaki、Junko Sone、Shinya Tsutsumi、Toshiyuki Kosaka、Koji Abe、Satoshi Kimura、Kaoru Shimada

  DOI：10.1021/jm970658w

  日期：1998.9.1

  A series of hexadeoxyribonucleotides (6-mers), d(TGGGAG), substituted with a variety of aromatic groups at the 5'-end were synthesized and tested for anti-human immunodeficiency virus type 1 (HIV-1) activity. While unmodified d(TGGGAG) (31) had no anti-HIV-l activity, compound 23 with a 3,4-di(benzyloxy)benzyl (DBB) group at the 5'-end potently inhibited the HIV-1(IIIB)-induced cytopathicity of MT-4 cells in vitro (IC50 = 0.37 mu M) without cytotoxicity up to 40 mu M. A thermal denaturation study on the 5'-end-substituted 6-mers by means of the circular dichroism (CD) spectra demonstrated that the aromatic substituent attached at the 5'-end of the 6-mer strongly enhanced the formation of a parallel helical structure consisting of four strands (quadruplex). On the contrary, compound 36, in which one of the guanosines of 23 was replaced by a thymidine, did not form a quadruplex, thus exhibiting no anti-HIV-1 activity. Moreover, both compound 15, with a tert-butyldiphenylsilyl group solely at its 3'-end, and compound 21, with a relatively small substituent, a benzyl group, at the 5'-end, formed quadruplexes but had no anti-HIV-1 activity. These findings led us to the conclusion that both the quadruplex structure and the aromatic substituent with adequate size at the 5'-end are crucial for the interaction of the 5'-end-substituted 6-mers with the V3 loop as well as the CD4 binding site on viral gp120, resulting in anti-HIV-1 activity.