bis(2-<4-nitrophenyl>ethyl) N,N-diisopropylphosphoramidite | 102690-87-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: bis(2-<4-nitrophenyl>ethyl) N,N-diisopropylphosphoramidite
• 英文别名: di-2-(4-nitrophenyl)ethoxy-N,N-diisopropyl phosphoramidite；di(p-nitrophenethyl) diisopropylphosphoramidite；N-[bis[2-(4-nitrophenyl)ethoxy]phosphanyl]-N-propan-2-ylpropan-2-amine
• CAS: 102690-87-9
• 化学式: C₂₂H₃₀N₃O₆P
• 分子量: 463.47
• InChiKey: WBVCNMMEIPRPQP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.67
• 重原子数：
  32.0
• 可旋转键数：
  13.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  107.98
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  bis(2-<4-nitrophenyl>ethyl) N,N-diisopropylphosphoramidite 在 四氮唑 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 7.0h， 生成 3'-[[bis[2-(4-nitrophenyl)ethoxy]phosphinyl]oxy]-5'-[2-[(N-fluorenemethyloxycarbonyl)-aminooxy]]-acetylamino-N-benzoyl-2',5'-dideoxyadenosine
  参考文献：
  名称：

  A Library Approach to the Generation of Bisubstrate Analogue Sulfotransferase Inhibitors

  摘要：

  [GRAPHICS]A library of potential bisubstrate analogue inhibitors (1) targeting sulfotransferase enzymes was generated by the chemoselective ligation of the PAPS mimic 2 with a panel of 447 aldehydes. Preliminary screening has identified compounds that inhibit estrogen sulfotransferase (EST), an enzyme relevant to breast cancer.

  DOI：

  10.1021/ol0162217
• 作为产物：
  描述：

  二异丙胺 在 N,N-二异丙基乙胺 、 三氯化磷 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 3.0h， 生成 bis(2-<4-nitrophenyl>ethyl) N,N-diisopropylphosphoramidite
  参考文献：
  名称：

  Synthesis of Deoxyadenosine 3‘-Phosphates Bearing Cis and Trans Adducts of 7β,8α-Dihydroxy-9α,10α-epoxy-7,8,9,10-tetrahydrobenzo[a]pyrene:  Standards for ³²P-Postlabeling Assays

  摘要：

  Deoxyadenosine 3'-phosphates bearing cis and trans N-6 adducts of (7R) and (7S)-anti 7 beta,8 alpha-dihydroxy-9 alpha,10 alpha-epoxy-7,8,9, 10-tetrahydrobenzo[alpha]pyrenes have been prepared in good yield by reaction of 6-fluoropurinyl 2'-deoxyriboside 3'-(bis(2-[4-nitrophenyl]ethyl)phosphate with the (+/-)(7 beta,8 alpha,9 alpha,10 beta)- and (+/-)-(7 beta,8 alpha,9 alpha,10 alpha)-10-amino-7,8,9,10-tetrahydrobenzo[alpha]pyrene-7,8,9-triols. The protected phosphates are easily prepared as diasteromeric mixtures, readily resolved by reversed phase HPLC, and efficiently deprotected with DBU to give the adducted S'-phosphates. These nucleotides are of value as standards for the P-32-postlabeling procedure of Randerath for determination of benzo[alpha]pyrene adducts in DNA (Reddy et al. Carcinogenesis 1984, 5, 231).

  DOI：

  10.1021/jo9510898

文献信息

• Chemical 5′-phosphorylation of oligonucleotidesvaluable in automated DNA synthesis
  作者：E. Uhlmann、J. Engels

  DOI：10.1016/s0040-4039(86)80038-7

  日期：1986.1

  for the chemical 5′-phosphorylation ofoligonucleotides starting from easily available phosphorous-III compounds using phosphate protecting groups which can be cleaved off via β-elimination. The hydrophobic 2-(p-nitrophenyl)-ethyl group, at the phosphodiester level can serve as a purification handle in reversed phase HPLC. Moreover, the procedure has been adapted to automated DNA synthesis.

  已经开发了一种新的化学寡核苷酸5'-磷酸化的新方法，该方法使用易于通过β-消除作用裂解的磷酸酯保护基，从易于获得的III族磷化合物开始。磷酸二酯水平的疏水性2-（对硝基苯基）-乙基可以用作反相HPLC中的纯化操作。此外，该程序已适应于自动DNA合成。
• 5-Enolpyruvylshikimate 3-Phosphate Synthase:  Chemical Synthesis of the Tetrahedral Intermediate and Assignment of the Stereochemical Course of the Enzymatic Reaction
  作者：Ming An、Uday Maitra、Ulf Neidlein、Paul A. Bartlett

  DOI：10.1021/ja036627+

  日期：2003.10.1

  been accomplished. Combination of methyl dibromopyruvate with a protected shikimic acid derivative, phosphorylation, and lactonization afforded the intermediates (S)-15 and (R)-15, whose configurations were assigned by NMR. After introduction of the 3-phosphate group and deprotection, photoinitiated radical debromination of the dibromo analogues (S)-5 and (R)-5 was accomplished with tributyltin hydride

  参与 5-enolpyruvylshikimate 3-磷酸合酶 (EPSPS) 催化的四面体中间体的两种非对映异构体的化学合成已经完成。二溴丙酮酸甲酯与受保护的莽草酸衍生物的组合、磷酸化和内酯化得到中间体 (S)-15 和 (R)-15，其构型由 NMR 指定。在引入 3-磷酸基团和脱保护后，在表面活性剂的存在下，在混合水性溶剂中用三丁基氢化锡完成二溴类似物 (S)-5 和 (R)-5 的光引发自由基脱溴，得到丙酮酸缩酮磷酸盐（ R)-TI 和 (S)-TI，分别。这些化合物在高 pH 值下稳定，但在 pH 值 7 时分解，半衰期约为 10 分钟。(R)-TI 被证明对 EPSPS 是惰性的，而 (S)-TI 被酶转化为 5-烯醇丙酮酸莽草酸 3-磷酸、莽草酸 3-磷酸和磷酸烯醇丙酮酸的混合物。酶中间体在缩酮中心具有 S 构型的证明证实了作为反加成和顺式消除的机制。此外，似乎第二步的顺式