Robin's reagent | 138373-37-2

• 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: Robin's reagent
• 英文别名: [2-[acetyl(trimethylsilyl)amino]-9-trimethylsilylpurin-6-yl] N,N-diphenylcarbamate
• CAS: 138373-37-2
• 化学式: C₂₆H₃₂N₆O₃Si₂
• 分子量: 532.749
• InChiKey: OBOWPHZEYHJOTE-UHFFFAOYSA-N

物化性质

• 沸点：
  604.7±65.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.03
• 重原子数：
  37
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  93.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Robin's reagent 在 ammonium hydroxide 、 三氟甲磺酸三甲基硅酯 、 溶剂黄146 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 72.0h， 生成 9-((1R,2R,3S)-tetrahydro-2-hydroxy-3-hydroxymethyl-1-furanyl)-9H-guanine
  参考文献：
  名称：

  一系列亚甲基膨胀的氧色霉素核苷类似物的合成和生物活性

  摘要：

   一系列的亚甲基-奥塔诺扩大核苷类似物， 例如 类似物 2 和已知的抗病毒的核苷 AZT ， FLT ，和 的ddC （ 3 ）通过用容易获得的（开始非常直接的路线制备 小号  ） -缩水甘油 4 和程序 经由 所述二氢呋喃-3-甲醇 9a ， b 。这些修饰核苷的生物学测试表明，它们是无细胞毒性的化合物，通常具有较弱的抗病毒活性。但是，鸟苷类似物 2G 表现出明显的活性 与 。单纯疱疹病毒1型（HSV-1）在细胞培养中，并且是HSV-1编码的胸苷激酶依赖性的。因此，该化合物是开发新的抗HSV药物的有趣的新先导结构。

  DOI：

  10.1007/s007060200024
• 作为产物：
  描述：

  N,O-双三甲硅基乙酰胺 、 N,N-二苯基-氨基甲酸 2-(乙酰氨基)-9H-嘌呤-6-基酯 以 1,2-二氯乙烷 为溶剂， 反应 0.25h， 生成 Robin's reagent
  参考文献：
  名称：

  一系列亚甲基膨胀的氧色霉素核苷类似物的合成和生物活性

  摘要：

   一系列的亚甲基-奥塔诺扩大核苷类似物， 例如 类似物 2 和已知的抗病毒的核苷 AZT ， FLT ，和 的ddC （ 3 ）通过用容易获得的（开始非常直接的路线制备 小号  ） -缩水甘油 4 和程序 经由 所述二氢呋喃-3-甲醇 9a ， b 。这些修饰核苷的生物学测试表明，它们是无细胞毒性的化合物，通常具有较弱的抗病毒活性。但是，鸟苷类似物 2G 表现出明显的活性 与 。单纯疱疹病毒1型（HSV-1）在细胞培养中，并且是HSV-1编码的胸苷激酶依赖性的。因此，该化合物是开发新的抗HSV药物的有趣的新先导结构。

  DOI：

  10.1007/s007060200024

文献信息

• Regioisomers in Vorbrüggen's guanine nucleoside synthesis; N9 selectivity with a glucosamine derivative and 2-N-acetyl-6-O-diphenylcarbamoylguanine
  作者：Minghong Zhong、Morris J. Robins

  DOI：10.1016/j.tetlet.2003.10.070

  日期：2003.12

  Vorbrüggen coupling of trimethylsilylated 2-N-acetylguanine with pentofuranose derivatives gives N7/N9 glycosyl mixtures. The N9 isomers can be obtained selectively with 2-N-acetyl-6-O-diphenylcarbamoylguanine, and even with a less reactive glucosamine derivative.

  三甲基甲硅烷基化的2- N-乙酰鸟嘌呤与戊呋喃糖衍生物的伏尔布吕根偶联产生N7 / N9糖基混合物。N9异构体可以用2 - N-乙酰基-6- O-二苯基氨基甲酰基鸟嘌呤，甚至用反应性较低的葡糖胺衍生物选择性地获得。
• Efficient synthesis of α-purine nucleosides of 2-deoxyribofuranose and 2-deoxyribopyranose
  作者：Selvasekaran Janardhanam、Krishnan P. Nambiar

  DOI：10.1039/c39940001009

  日期：——

  A high yield synthesis of α-purine nucleosides of 2-deoxyribofuranose and 2-deoxyribopyranose is reported starting from 1,3,5-tri-O-acetyl-2-deoxyribofuranose and 1,3,5,-tri-O-acetyl-2-deoxyribopyranose with silylated purines under Lewis acid (SnCl4) catalysed conditions.

  据报道，在路易斯酸（SnCl4）催化条件下，从1,3,5-三-O-乙酰基-2-脱氧呋喃核糖和1,3,5-三-O-乙酰基-2-脱氧吡喃核糖出发，在硅烷化的嘌呤作用下，可以合成高产量的β-嘌呤核苷。
• Nucleotides. LXXIV Synthesis of a-D-Arabino-oligonucleotides
  作者：Christoph Henke、Wolfgang Pfleiderer

  DOI：10.1080/15257770500267113

  日期：2005.9.1

  The 5 alpha-D-arabinofuranosylnucleosides alpha-araU (15), alpha-araT (18), alpha-araC (22), alpha-araA (25), and alpha-araG (28) have been synthesized by the modified silyl-method. The amino groups at the nucleobases and the 2'-hydroxy group at the sugar moiety were protected by the 2-(4-nitro-phenyl) ethoxycarbonyl (npeoc) group (37-40) and the amide function in alpha-araG was additionally blocked by the 2-(4-nitrophenyl)ethyl group (63) to improve solubility in organic solvents. Mono-and dimethoxytritylation of the 5'-OH group was performed in the usual manner to give 41-48, 64, and 65 in high yields and further substitution of the 3'-OH group led to the monomeric building blocks 66-75 as well as the 3'-O-succinoyl derivatives 76-85 functioning as starting units in solid-support oligonucleotide synthesis. A large number of oligo-alpha-arabinonucleotides have been prepared on modified CPG-material applying the npeoc/npe strategy as a very efficient synthetic tool for highly purified, homogenous oligomers. Hybridizations between alpha-arabinonucleotide strands revealed in analogy to earlier findings an antiparallel orientation whereas the combination of an oligo-alpha-D-arabinonucleotide with a complementary oligo-2'-deoxy-beta-D-ribofuranosylnucleotide showed base-pairing only if a parallel polarity was present. The advantages in oligo-alpha-arabinonucleotide synthesis were furthermore demonstrated by the synthesis of the t alpha-ANA(his) a structural analog of the natural tRNA(his) of the phage T5.
• Diastereoselective Synthesis ofN,O-Psiconucleosides, a New Class of Modified Nucleosides
  作者：Ugo Chiacchio、Antonino Corsaro、Venerando Pistarà、Antonio Rescifina、Daniela Iannazzo、Anna Piperno、Giovanni Romeo、Roberto Romeo、Giovanni Grassi

  DOI：10.1002/1099-0690(200204)2002:7<1206::aid-ejoc1206>3.0.co;2-0

  日期：2002.4
• An unusual solvent effect on the regiochemical outcome (N-9 versus N-7) of guanine glycosylation using Robins' reagent (2-N-acetyl-6-O-diphenylcarbamoylguanine)
  作者：Adrian Wai-Hing Cheung、Achyutharao Sidduri、Lisa M Garofalo、Robert A Goodnow

  DOI：10.1016/s0040-4039(00)00423-8

  日期：2000.4

  An unexpectedly low N-9/N-7 regioselectivity was obtained when Robins' reagent (2-N-acetyl-6-O-diphenylcarbamoylguanine) was coupled with a D-glucosamine derivative under trimethylsilyl trifluoromethanesulfonate activation. An unprecedented solvent effect (toluene versus dichloroethane) on the N-9/N-7 ratio was also observed in the same study. The use of 2-N-acetyl-6-O-benzylguanine to successfully overcome the above regioselectivity problem is described. (C) 2000 Elsevier Science Ltd. All rights reserved.