Diisopropyl-phosphoramidous acid (2R,3R,4R,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-(tert-butyl-dimethyl-silanyloxy)-5-[6-(2-phenoxy-acetylamino)-purin-9-yl]-tetrahydro-furan-3-yl ester 2-cyano-ethyl ester | 121058-86-4

• 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: Diisopropyl-phosphoramidous acid (2R,3R,4R,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-(tert-butyl-dimethyl-silanyloxy)-5-[6-(2-phenoxy-acetylamino)-purin-9-yl]-tetrahydro-furan-3-yl ester 2-cyano-ethyl ester
• 英文别名: (2R,3R,4R,5R)-2-((Bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-4-((tert-butyldimethylsilyl)oxy)-5-(6-(2-phenoxyacetamido)-9H-purin-9-yl)tetrahydrofuran-3-yl (2-cyanoethyl) diisopropylphosphoramidite；N-[9-[(2R,3R,4R,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-3-[tert-butyl(dimethyl)silyl]oxy-4-[2-cyanoethoxy-[di(propan-2-yl)amino]phosphanyl]oxyoxolan-2-yl]purin-6-yl]-2-phenoxyacetamide
• CAS: 121058-86-4
• 化学式: C₅₄H₆₈N₇O₉PSi
• 分子量: 1018.23
• InChiKey: DBCNFFIOULAURJ-NMRDYAFNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.82
• 重原子数：
  72
• 可旋转键数：
  24
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  174
• 氢给体数：
  1
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  Diisopropyl-phosphoramidous acid (2R,3R,4R,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-(tert-butyl-dimethyl-silanyloxy)-5-[6-(2-phenoxy-acetylamino)-purin-9-yl]-tetrahydro-furan-3-yl ester 2-cyano-ethyl ester 在 甲胺 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 以78%的产率得到
  参考文献：
  名称：

  O-Selective Condensation Using P−N Bond Cleavage in RNA Synthesis without Base Protection

  摘要：

  In RNA synthesis without base protection, a new method for O-selective condensation with more than 99% selectivity was developed by 6-nitro-HOBt-mediated cleavage of undesired P(III)-N bonds on nucleobase moieties. Moreover, we for the first time succeeded in synthesizing oligoRNAs without base protection.

  DOI：

  10.1021/ol800911b
• 作为产物：
  描述：

  腺苷 在 4-二甲氨基吡啶 咪唑 、 1-羟基苯并三唑 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 吡啶 、 乙腈 为溶剂， 反应 20.0h， 生成 Diisopropyl-phosphoramidous acid (2R,3R,4R,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-(tert-butyl-dimethyl-silanyloxy)-5-[6-(2-phenoxy-acetylamino)-purin-9-yl]-tetrahydro-furan-3-yl ester 2-cyano-ethyl ester
  参考文献：
  名称：

  不稳定碱基保护基在寡核糖核苷酸合成中的应用

  摘要：

  描述了在通过氰基乙基亚磷酰胺方法合成寡核苷酸中，苯氧基乙酰基用于保护嘌呤碱基的环外氨基官能团和乙酰基用于胞嘧啶。在加盖步骤中观察到了副反应，即被保护的鸟嘌呤的苯氧基乙酰基部分被乙酰基部分取代。可以通过使用苯氧乙酸酐代替乙酸酐来避免这种情况。

  DOI：

  10.1016/s0040-4039(01)80326-9

文献信息

• Nucleoside recovery in DNA and RNA synthesis
  作者：Weimin Wang、Quanlai Song、Roger A. Jones

  DOI：10.1016/s0040-4039(99)01914-0

  日期：1999.12

  Nucleoside phosphoramidites and H-phosphonate diesters can be converted to nucleosides under mild conditions and in high yields by reaction with polyhydroxy alcohols. (C) 1999 Elsevier Science Ltd. All rights reserved.
• CHAIX, CAROLE;MOLKO, DIDIER;TEOULE, ROBERT, TETRAHEDRON LETT., 30,(1989) N 1, C. 71-74
  作者：CHAIX, CAROLE、MOLKO, DIDIER、TEOULE, ROBERT

  DOI：——

  日期：——
• The use of labile base protecting groups in oligoribonucleotide synthesis
  作者：Carole Chaix、Didier Molko、Robert Téoule

  DOI：10.1016/s0040-4039(01)80326-9

  日期：——

  The use of phenoxyacetyl group for the protection of the exocyclic amino function of purine bases and acetyl group for cytosine in oligonucleotide synthesis by the cyanoethylphosphoramidite approach is described. A side reaction - i.e. partial replacement of phenoxyacetyl group of protected guanines by acetyl group - was observed during the capping step. It can be avoided by the use of phenoxyacetic

  描述了在通过氰基乙基亚磷酰胺方法合成寡核苷酸中，苯氧基乙酰基用于保护嘌呤碱基的环外氨基官能团和乙酰基用于胞嘧啶。在加盖步骤中观察到了副反应，即被保护的鸟嘌呤的苯氧基乙酰基部分被乙酰基部分取代。可以通过使用苯氧乙酸酐代替乙酸酐来避免这种情况。
• <i>O</i>-Selective Condensation Using P−N Bond Cleavage in RNA Synthesis without Base Protection
  作者：Akihiro Ohkubo、Yasukazu Kuwayama、Tomomi Kudo、Hirosuke Tsunoda、Kohji Seio、Mitsuo Sekine

  DOI：10.1021/ol800911b

  日期：2008.7.3

  In RNA synthesis without base protection, a new method for O-selective condensation with more than 99% selectivity was developed by 6-nitro-HOBt-mediated cleavage of undesired P(III)-N bonds on nucleobase moieties. Moreover, we for the first time succeeded in synthesizing oligoRNAs without base protection.