9-三甲硅基-6-[(三甲硅基)氧]基-9H-嘌呤 | 17962-89-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 中文名称: 9-三甲硅基-6-[(三甲硅基)氧]基-9H-嘌呤
• 英文名称: 9-(trimethylsilyl)-6-[(trimethylsilyl)oxy]-9H-purine
• 英文别名: O,N⁹-bis(trimethylsilyl)hypoxanthine；9-trimethylsilanyl-6-trimethylsilanyloxy-9H-purine；9H-Purine, 9-(trimethylsilyl)-6-[(trimethylsilyl)oxy]-；trimethyl-(6-trimethylsilyloxypurin-9-yl)silane
• CAS: 17962-89-9
• 化学式: C₁₁H₂₀N₄OSi₂
• 分子量: 280.477
• InChiKey: GQQMYRBRLIEVPC-UHFFFAOYSA-N

物化性质

• 保留指数：
  1794;1792;1793;1796;1798

计算性质

• 辛醇/水分配系数(LogP)：
  2.72
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  52.8
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  9-三甲硅基-6-[(三甲硅基)氧]基-9H-嘌呤 在 氨 、 四氯化锡 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 生成 9-(6'-deoxy-α-L-talofuranosyl)hypoxanthine
  参考文献：
  名称：

  Synthesis and antitumor activity of 7- and 9-(6'-deoxy-.alpha.-L-talofuranosyl)-hypoxanthine and 9-(6'-deoxy-.alpha.-L-talofuranosyl)-6-thiopurine

  摘要：

  Reaction of 6-deoxy-2,3,5-tris-O-(p-nitrobenzoyl)-L-talofuranosyl bromide (1) with the trimethylsilyl derivative of hypoxanthine, followed by removal of blocking groups, afforded 9- (6) and 7-(6'-deoxy-alpha-L-talofuranosyl)hypoxanthine (7). A study of the published optical rotations and circular dichroic (CD) spectra of pentofuranosylpurines and of (6'-deoxy-beta-D-allo- and -alpha-L-talofuranosyl)purines prepared here suggests that the sign of rotation and the sign of the longer wavelength Cotton effect is determined solely by the configuration of C-1' and its position of attachment to the purine ring. For C-1' R nucleosides, the sign is negative for N-9-linked purine nucleosides and positive for the N-7-linked isomers, and vice versa for C-1'S purine nucleosides. Reaction of 1 with the trimethylsilyl derivative of 6-chloropurine afforded 4, which upon treatment with thiourea and deblocking yielded 9-(6'-deoxy-alpha-L-talofuranosyl)-6-thiopurine (8). Unlike the previously prepared 7-(6'-deoxy-beta-D-allofuranosyl) hypoxanthine which strongly inhibited purine nucleoside phosphorylase, compounds 6-8 did not inhibit this enzyme. Compound 8 significantly inhibited the growth of L1210 tumor cells in vitro and in vivo.

  DOI：

  10.1021/jm00364a032
• 作为产物：
  描述：

  六甲基二硅氮烷 、 次黄嘌呤 在 chitosan-silica sulfate nanohybrid 作用下， 反应 1.17h， 以100%的产率得到9-三甲硅基-6-[(三甲硅基)氧]基-9H-嘌呤
  参考文献：
  名称：

  壳聚糖-硫酸硅纳米杂化物：一种高效的绿色多相纳米催化剂，可通过预硅烷化方法区域选择性合成N-烷基嘌呤，嘧啶和相关的N-杂环

  摘要：

  摘要描述了利用壳聚糖-硫酸硅纳米杂化物（CSSNH）用HMDS对嘌呤和嘧啶核苷碱基以及其他相关的N-杂环进行甲硅烷基化。事实证明，CSSNH是一种有用，高效且生态友好的异质纳米杂化催化剂，可用于核碱基的甲硅烷基化。然后使预甲硅烷基化的核碱基与不同来源的碳亲电试剂反应，以良好至优异的产率得到所需的N-烷基取代的衍生物。CSSNH展示了一些优势，包括易于处理和准备，低成本，可重复使用性以及对环境的友好性。这些独特的特性使CSSNH成为绿色工业过程中的理想选择。 图形摘要

  DOI：

  10.1007/s11696-019-00863-1

文献信息

• Total Synthesis of <i>N</i>-Malayamycin A and Related Bicyclic Purine and Pyrimidine Nucleosides
  作者：Stephen Hanessian、Guobin Huang、Caroline Chenel、Roger Machaalani、Olivier Loiseleur

  DOI：10.1021/jo050727b

  日期：2005.8.1

  synthesis of bicyclic perhydrofuropyran nucleosides as N-analogues of the naturally occurring malayamycin A. Formation of the N-nucleosides relied on the activation of thioglycosides, proceeding via sulfonium intermediates. Ring closure metathesis was used in two approaches to build the bicyclic dioxa heterocycle. Another approach relied on the use of a sugar precursor and cyclization to the bicyclic thioglycoside

  方法双环perhydrofuropyran核苷的全合成被描述为Ñ -analogues所述的天然存在的malayamycin A.形成的Ñ核苷依靠硫代糖苷的激活，经由锍中间体进行。闭环复分解用于两种方法来构建双环二氧杂环杂环。另一种方法依赖于糖前体的使用和环化成双环硫代糖苷。
• Silica Sulfuric Acid (SSA) as a Highly Efficient Heterogeneous Catalyst for Persilylation of Purine and Pyrimidine Nucleobases and Other <i>N</i>-Heterocycles Using Hmds
  作者：Mohammad Navid Soltani Rad、Ali Khalafi-Nezhad、Masoumeh Divar、Somayeh Behrouz

  DOI：10.1080/10426500903383952

  日期：2010.8.25

  Purine and pyrimidine nucleobases and other N-heterocycles have been silylated with HMDS in excellent yields in the presence of a catalytic amount of silica sulfuric acid (SSA) as a heterogeneous catalyst. SSA utilizes a shorter reaction time and higher yields of silylated nucleobases. SSA is reusable for several times without a decrease in reactivity or yield of silylated adducts.
• Kraska, Burckhard; Lichtenthaler, Frieder W., Chemische Berichte, 1981, vol. 114, # 5, p. 1636 - 1648
  作者：Kraska, Burckhard、Lichtenthaler, Frieder W.

  DOI：——

  日期：——
• Synthesis of hypoxanthine, guanine, and 6-thiopurine nucleosides of 6-deoxy-D-allofuranose
  作者：Victor Nelson、Hassan S. El Khadem、Bertwell K. Whitten、Debra Sesselman

  DOI：10.1021/jm00361a023

  日期：1983.7

  Hypoxanthine, guanine, and 6-thiopurine nucleosides of 6-deoxy-D-allofuranose have been prepared as potential antitumor agents. Thus, reaction of 6-deoxy-beta-D-allofuranosyl bromide (1) with the trimethylsilyl derivatives of hypoxanthine and guanine afforded mixtures of the 9- and the 7-substituted bases, which were separated and deblocked with ammonia to give 9-(6'-deoxy-beta-D-allofuranosyl)hypoxanthine (6), 7-(6'-deoxy-beta-D-allofuranosyl)hypoxanthine (7), 9-(6'-deoxy-beta-D-allofuranosyl)guanine (8), and 7-(6'-deoxy-beta-D-allofuranosyl)guanine (9). The two nucleosides with the purine joined at the N-9 position, namely, 6 and 8, are easily distinguished from the other two nucleosides (7 and 9), having N-7 junctions, by their NMR spectra. Reaction of 1 with the trimethylsilyl derivative of 6-chloropurine afforded 10, which upon treatment with thiourea and deblocking gave 9-(6'-deoxy-beta-D-allofuranosyl)-6-thiopurine (12). The hypoxanthine and guanine nucleosides showed no inhibition of mouse leukemia L1210 when tested in vivo, but the thiopurine nucleoside 12 showed strong inhibition of growth of L1210 both in vivo and in vitro. Compound 7 strongly inhibited purine nucleoside phosphorylase (KI = 8.8 X 10(-5) M), while compounds 8, 9, 6, and 12 were inactive.
• Analogs of purine nucleosides. 3. Alkoxyalkylation of hypoxanthine by the silyl method
  作者：M. A. Madre、�. �. Liepin'sh、R. A. Zhuk、O. V. Sakhartova、M. Yu. Lidak

  DOI：10.1007/bf00542784

  日期：1986.4