6-iodo-9-(2-deoxy-3,5-di-(tert-butyldimethylsilyloxy)-β-D-erythro-pentofuranosyl)purine | 135419-06-6

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: 6-iodo-9-(2-deoxy-3,5-di-(tert-butyldimethylsilyloxy)-β-D-erythro-pentofuranosyl)purine
• 英文别名: 6-iodo-9-[3,5-bis-O-(tert-butyldimethylsilyl)-2-deoxy-β-D-erythro-pentofuranosyl]purine；6-iodo-9-[2-deoxy-3,5-bis-O-(tert-butyldimethylsilyl)β-D-erythro-pentafuranosyl]purine；6-Iodo-9-<3,5-di-O-(tert-butyldimethylsilyl)-β-D-ribofuranosyl>purine；3',5'-bis-O-(tert-butyldimethylsilyl)-6-deamino-2'-deoxy-6-iodoadenosine；6-Iodo-9-[3,5-di-O-(tert-butyldimethylsilyl)-β-D-ribofuranosyl]purine；tert-butyl-[[(2R,3S,5R)-3-[tert-butyl(dimethyl)silyl]oxy-5-(6-iodopurin-9-yl)oxolan-2-yl]methoxy]-dimethylsilane
• CAS: 135419-06-6
• 化学式: C₂₂H₃₉IN₄O₃Si₂
• 分子量: 590.652
• InChiKey: HXACUVWHDVJFGU-GVDBMIGSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.13
• 重原子数：
  32
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  71.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  6-iodo-9-(2-deoxy-3,5-di-(tert-butyldimethylsilyloxy)-β-D-erythro-pentofuranosyl)purine 在 palladium on activated charcoal 、 tris(dibenzylideneacetone)dipalladium (0) copper(l) iodide 、 三苯胂 、 氢气 、 triethylamine tris(hydrogen fluoride) 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 17.75h， 生成 (S)-3-{4-[9-(2-deoxy-β-D-erythro-pentofuranosyl)purin-6-yl]phenyl}-2-aminopropanoic acid
  参考文献：
  名称：

  对映体纯（Purin-6-基）苯丙氨酸及其核苷，一种新型的嘌呤氨基酸缀合物的合成。

  摘要：

  对映体或非对映体纯的4-（嘌呤-6-基）苯丙氨酸，一种新型的稳定氨基酸-嘌呤偶联物，是通过钯催化的受保护的4-硼硼烷苯丙氨酸或4-（三甲基锡烷基）苯丙氨酸与不同的交叉偶联反应而合成的。 6-卤尿嘧啶（9-苄基-6-卤尿嘧啶和9-（四氢吡喃-2-基）-6-卤尿嘧啶以及酰基和甲硅烷基保护的6-卤代嘌呤核糖核苷和2-脱氧核糖核苷）。交叉偶联反应产物完全脱保护后，获得6位带有（S）-或（R）-苯丙氨酸的游离嘌呤碱基和核苷。这些交叉偶联和脱保护方案的反应性趋势已在实用性，效率和立体选择性方面进行了比较。

  DOI：

  10.1021/jo051110x
• 作为产物：
  描述：

  9-((2R,4S,5R)-4-((叔丁基二甲基硅烷基)氧基)-5-(((叔丁基二甲基硅烷基)氧基)甲基)四氢呋喃-2-基)-9H-嘌呤-6-胺 在 二碘甲烷 、 亚硝酸正戊酯 作用下， 反应 1.0h， 以62%的产率得到6-iodo-9-(2-deoxy-3,5-di-(tert-butyldimethylsilyloxy)-β-D-erythro-pentofuranosyl)purine
  参考文献：
  名称：

  Cosstick, Richard; Douglas, Mark E., Journal of the Chemical Society. Perkin transactions I, 1991, # 5, p. 1035 - 1040

  摘要：

  DOI：

文献信息

• Synthesis of (purin-6-yl)methylphosphonate bases and nucleosides
  作者：Zbyněk Hasník、Radek Pohl、Michal Hocek

  DOI：10.1016/j.tetlet.2010.02.167

  日期：2010.5

  the synthesis of the title (purin-6-yl)methylphosphonates were investigated and compared. While, the Arbuzov reaction of 6-(iodomethyl)purines with triethyl phosphite did not work, Michaelis–Becker alkylation of the sodium salt of diethyl phosphonate with 6-(mesyloxymethyl)purines gave the desired products in good yields. The best method was based on Rh- or Pd-catalyzed cross-coupling reactions of 6-iodopurines

  研究和比较了标题（嘌呤-6-基）甲基膦酸酯的三种合成方法。虽然6-（碘甲基）嘌呤与亚磷酸三乙酯的Arbuzov反应不起作用，但膦酸二乙酯钠盐与6-（甲磺酰氧基甲基）嘌呤的Michaelis-Becker烷基化反应却以高收率得到了所需的产物。最好的方法是基于6-碘嘌呤与（二异丙氧基磷酰基甲基）溴化锌的Rh或Pd催化的交叉偶联反应。以这种方式以高收率制备了少量的6-（二异丙氧基磷酰基甲基）嘌呤碱和核苷。
• Chemical Synthesis of Cross-Linked Purine Nucleosides
  作者：Francesco De Riccardis、Francis Johnson

  DOI：10.1021/ol990351m

  日期：2000.2.1

  efficient route to all of the possible cross-linked 2'-deoxypurines 1-3 has been developed by means of the Pd-mediated C-N bond formation in the key step. Utilizing this protocol, the synthesis of the first unnatural protected purine trimeric adduct 4 has been accomplished.

  [反应：见正文]在关键步骤中，通过Pd介导的CN键的形成，已经开发出一种有效的途径来连接所有可能的交联2'-脱氧嘌呤1-3。利用该方案，已经完成了第一个非天然的受保护的嘌呤三聚体加合物4的合成。
• Design and synthesis of novel photoinduced electron transfer-based hybridization probes
  作者：Chika Yokoyama、Kosuke Nakamoto、Yoshihito Ueno

  DOI：10.1016/j.bmc.2017.05.013

  日期：2017.7

  Photoinduced electron transfer (PeT)-based hybridization probe is a linear and quencher-free oligonucleotide (ON) probe for DNA or RNA detection. In this report, we designed and synthesized novel adenosine analogues for PeT-based hybridization probe. In particular, the analogue containing a piperazinomethyl moiety showed effective quenching property under physiological conditions. When the probe containing the analogue was hybridized with a complementary DNA or RNA, the fluorescence increased 3- or 4-fold, respectively, compared to the single-stranded state. (C) 2017 Elsevier Ltd. All rights reserved.
• Photoinduced Electron-Transfer-Based Hybridization Probes for Detection of DNA and RNA
  作者：Kan Takahashi、Shun Ito、Kosuke Nakamoto、Yasutomo Ito、Yoshihito Ueno

  DOI：10.1021/acs.joc.5b01132

  日期：2015.9.4

  Here, we report the synthesis of a hybridization probe for detection of RNA and DNA based on photoinduced electron transfer (PeT). We designed and synthesized an oligonucleotide containing an adenosine analogue with a 9-(N,N-dimethylaminomethyl)anthracenyl moiety at its 6-position via an ethynylene linker as the hybridization probe. When the probe was hybridized with a complementary RNA or DNA, the fluorescence intensity increased 3-fold or 4.5-fold, respectively, compared to the single-stranded state.
• COSSTICK, RICHARD;DOUGLAS, MARK E., J. CHEM. SOC. PERKIN TRANS. 1,(1991) N, C. 1035-1040
  作者：COSSTICK, RICHARD、DOUGLAS, MARK E.

  DOI：——

  日期：——