5’-[(2-cyanoethyl)(N,N-diisopropyl)]phosphoramidite-3′-O-acetylthymidine | 143446-82-6

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 核苷和核苷酸类似物
• 英文名称: 5’-[(2-cyanoethyl)(N,N-diisopropyl)]phosphoramidite-3′-O-acetylthymidine
• 英文别名: Acetic acid (2R,3S,5R)-2-[(2-cyano-ethoxy)-diisopropylamino-phosphanyloxymethyl]-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester；N(iPr)2P(OCH2CH2CN)(-5)2-deoxy-D-eryPenf3Ac(b)-thymin-1-yl；[(2R,3S,5R)-2-[[2-cyanoethoxy-[di(propan-2-yl)amino]phosphanyl]oxymethyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl] acetate
• CAS: 143446-82-6
• 化学式: C₂₁H₃₃N₄O₇P
• 分子量: 484.489
• InChiKey: TZEIFVDFXXSLJP-XPNOHXDVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  33
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  130
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  5’-[(2-cyanoethyl)(N,N-diisopropyl)]phosphoramidite-3′-O-acetylthymidine 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 、 5-(乙硫基)-1H-四唑 作用下， 以 乙腈 为溶剂， 反应 5.0h， 生成 thymidine 5′-(1,3-dimethylimidazolidin-2-ylidene)phosphate
  参考文献：
  名称：

  使用施陶丁格反应合成新的核苷 5'-α-亚氨基磷酸盐

  摘要：

  开发了使用施陶丁格反应合成新化合物 - 核苷 5'-α-亚氨基磷酸盐的有效方案。这些物质是 α-磷酸模拟核苷酸，其中氧原子被相应的亚氨基 (= N -R)-基团取代。获得了各种核苷的5'-亚氨基单磷酸盐。设计了一种基于亚氨基单磷酸酯的三磷酸酯衍生物的化学合成方法。合成了胸苷5'-(1,3-二甲基咪唑啉-2-亚基)-三磷酸(ppp(DMI)T)，首先研究了其与某些DNA聚合酶相关的水解稳定性和底物性质。结果表明，ppp(DMI)T可以作为人末端脱氧核苷酸转移酶TdT酶催化的不依赖模板的DNA合成的底物。

  DOI：

  10.1016/j.bioorg.2022.105987
• 作为产物：
  描述：

  2-氰乙基N,N-二异丙基氯亚磷酰胺 、 3'-O-acetylthymidine 在 三乙胺 作用下， 以 乙腈 为溶剂， 生成 5’-[(2-cyanoethyl)(N,N-diisopropyl)]phosphoramidite-3′-O-acetylthymidine
  参考文献：
  名称：

  Phosphorus deprotonation by a non-nucleophilic base is critical for the synthesis of nucleoside α-P-boranodiphosphates via a phosphoramidite approach

  摘要：

  Here we report the synthesis of nucleoside alpha-P-boranodiphosphate analogs via our improved phosphoramidite approach, where the addition of a non-nucleophilic base, TEA, to deprotonate phosphorus is considered to be critical to improve final product yields. Protonation on trivalent phosphorus might not only have blocked Lewis acid borane modification, but also have promoted byproduct formation through a trans-nucleophile process. Here, based on P-31 NMR data, mechanisms are proposed for P(V)-P(III) bond cleavage via phosphorus protonation-promoted nucleophile-exchange, and TEA deprotonation of phosphorus in promoting product formation in anhydrous synthetic reaction mixtures. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.08.047

文献信息

• SYNTHESIS OF NEW CLASSES OF BORON-CONTAINING NUCLEOTIDES
  作者：Jinlai Lin、Barbara Ramsay Shaw

  DOI：10.1081/ncn-100002335

  日期：2001.3.31

  Four different types of boron-modified nucleotides are reported: P-boranophosphorothioates, P-cyanoboranophosphates, P-boranomethylphosphonates, and P3'-N5'-boranophosphoramidates. Synthesis of dinucleoside borano-phosphorothioates and nucleoside P-borano-P-thiomonophosphates via a lithium sulfide method is described. The Li2S method also provides an alternative way to synthesize phosphorothioates through a dinitrophenyl P(V) phosphotriester precursor. The mechanism of Li2S substitution was investigated.
• Petra; De Boer; Koomen, Recueil des Travaux Chimiques des Pays-Bas, 1996, vol. 115, # 1, p. 99 - 102
  作者：Petra、De Boer、Koomen、Meeuwenoord、Kuyl-Yeheskiely、Van Der Marel、Van Boom

  DOI：——

  日期：——
• Tomasz, Jeno; Shaw, Barbara Ramsay; Porter, Ken, Angewandte Chemie, 1992, vol. 104, # 10, p. 1404 - 1406
  作者：Tomasz, Jeno、Shaw, Barbara Ramsay、Porter, Ken、Spielvogel, Bernard F.、Sood, Anup

  DOI：——

  日期：——