2'-O-tosylguanosine | 69370-84-9

• 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: 2'-O-tosylguanosine
• 英文别名: 2'-O-Tosylguanosine；[(2R,3R,4R,5R)-2-(2-amino-6-oxo-1H-purin-9-yl)-4-hydroxy-5-(hydroxymethyl)oxolan-3-yl] 4-methylbenzenesulfonate
• CAS: 69370-84-9
• 化学式: C₁₇H₁₉N₅O₇S
• 分子量: 437.433
• InChiKey: ZGTYELZJMKGCII-XNIJJKJLSA-N

物化性质

• 熔点：
  260-261 °C
• 密度：
  1.83±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  187
• 氢给体数：
  4
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2'-O-tosylguanosine 在 4-二甲氨基吡啶 、 叠氮化锂 、 三乙基硼氢化锂 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 89.0h， 生成 5'-O-benzoyl-3'-azido-2',3'-dideoxyguanosine
  参考文献：
  名称：

  Synthesis and anti-HIV activity of different sugar-modified pyrimidine and purine nucleosides

  摘要：

  A series of base-modified pyrimidine 3'-azido-2',3'-dideoxynucleosides and 3'-substituted purine and pyrimidine 2',3'-dideoxynucleosides have been synthesized and evaluated for their inhibitory activity against human immunodeficiency virus (HIV) replication in MT-4 cells. The following pyrimidine derivatives emerged as the most potent and/or selective inhibitors of HIV-induced cytopathogenicity (in order of decreasing selectivity: 3'-azido-3'-deoxythymidine (AZT), 3'-azido-2',3'-dideoxyuridine (AzddUrd), 3'-azido-2',3'-dideoxy-5-methylcytidine (AzddMeCyd), 3'-fluoro-ddUrd (FddUrd), 3'-fluoro-ddThd (FddThd), the N4-hydroxylated derivative of AzddMeCyd and the N4-methylated derivative of AzddMeCyd. Among the purine 2',3'-dideoxynucleosides, 3'-azido-2',3'-dideoxyguanosine (AzddGuo), 3'-fluoro-ddGuo (FddGuo), and 3'-fluoro-2,6-diaminopurine 2',3'-dideoxynucleoside (FddDAPR) were the most selective inhibitors of HIV replication.

  DOI：

  10.1021/jm00118a033
• 作为产物：
  描述：

  鸟苷 在 氨 作用下， 以 甲醇 为溶剂， 生成 2'-O-tosylguanosine
  参考文献：
  名称：

  Synthesis and anti-HIV activity of different sugar-modified pyrimidine and purine nucleosides

  摘要：

  A series of base-modified pyrimidine 3'-azido-2',3'-dideoxynucleosides and 3'-substituted purine and pyrimidine 2',3'-dideoxynucleosides have been synthesized and evaluated for their inhibitory activity against human immunodeficiency virus (HIV) replication in MT-4 cells. The following pyrimidine derivatives emerged as the most potent and/or selective inhibitors of HIV-induced cytopathogenicity (in order of decreasing selectivity: 3'-azido-3'-deoxythymidine (AZT), 3'-azido-2',3'-dideoxyuridine (AzddUrd), 3'-azido-2',3'-dideoxy-5-methylcytidine (AzddMeCyd), 3'-fluoro-ddUrd (FddUrd), 3'-fluoro-ddThd (FddThd), the N4-hydroxylated derivative of AzddMeCyd and the N4-methylated derivative of AzddMeCyd. Among the purine 2',3'-dideoxynucleosides, 3'-azido-2',3'-dideoxyguanosine (AzddGuo), 3'-fluoro-ddGuo (FddGuo), and 3'-fluoro-2,6-diaminopurine 2',3'-dideoxynucleoside (FddDAPR) were the most selective inhibitors of HIV replication.

  DOI：

  10.1021/jm00118a033

文献信息

• Study on disulfur-backboned nucleic acids: Part IV. Efficient synthesis of 3′,5′-dithio-2′-deoxyguanosine
  作者：Pei Hua Shang、Chang Mei Cheng、Hua Wang、Hong Chao Zheng、Yu Fen Zhao

  DOI：10.1016/j.cclet.2009.10.017

  日期：2010.2

  Abstract An efficient and novel method for synthesizing 3′,5′-dithio-2′-deoxyguanosine was described. In this method normal guanosine was used as the starting material. A very efficient procedure was used to synthesize 2- O -tosylguanosine 1 , which used 0.1 eq. DBTO instead of 2 eq. 1 was treated with LTBH to give 9-(2-deoxy- β - d -threo-pentofuranosyl)guanine 2 . 2 could be easily turned to the

  摘要描述了一种高效，新颖的3'，5'-二硫代-2'-脱氧鸟苷合成方法。在这种方法中，将正常的鸟苷用作起始原料。使用非常有效的程序来合成2-O-甲苯磺酰鸟苷1，其使用0.1eq.。DBTO代替2 eq。用LTBH处理1，得到9-（2-脱氧-β-d-苏-五氟呋喃糖基）鸟嘌呤2。2可以轻松地转化为目标化合物。
• Deoxygenative [1,2]-Hydride Shift Rearrangements in Nucleoside and Sugar Chemistry:  Analogy with the [1,2]-Electron Shift in the Deoxygenation of Ribonucleotides by Ribonucleotide Reductases¹
  作者：Morris J. Robins、Ireneusz Nowak、Stanislaw F. Wnuk、Fritz Hansske、Danuta Madej

  DOI：10.1021/jo071102b

  日期：2007.10.1

  semipinacol rearrangement that was observed in our laboratory has been applied to the synthesis of several furanose and pyranose derivatives. The process consists of an “orchestrated” [1,2]-hydride shift with departure of a leaving group from the opposite face. Transient formation of a CO group is followed by rapid transfer of a hydride-equivalent from the same face from which the leaving group departed

  在我们的实验室中观察到的半频哪醇重排的变体已应用于几种呋喃糖和吡喃糖衍生物的合成。该过程包括“精心策划的” [1,2]氢化物转移，同时离去基团从相反的表面离开。瞬态形成C O基团后，从离去基团离开的同一面快速转移氢化物当量，这导致两个邻位碳原子处的立体化学两次反转。2'治疗ö -和3'- ö -tosyladenosine与三乙基硼锂在DMSO / THF给出了与β-相应2'-和3'-脱氧核苷类似物d -苏型配置。相同的5'- O处理-TPS -2'- ö -tosyladenosine得到9-（5- ö -TPS-2-脱氧β- d -苏-pentofuranosyl）腺嘌呤。5'-OH和5'- O - TPS化合物具有相同的[1,2]-氢化物位移和立体化学，表明不存在远端羟基参与。将该方法应用于其他核苷2'- O-甲苯磺酰基衍生物，以良好的收率得到了2'-脱氧苏糖基化合物。对于2'- O
• Liu, Qi-Bin; Feng, Feng; Qu, Gui-Rong, Journal of Chemical Research - Part S, 2003, # 11, p. 706 - 707
  作者：Liu, Qi-Bin、Feng, Feng、Qu, Gui-Rong

  DOI：——

  日期：——
• HERDEWIJN, PIET;BALZARINI, JAN;BADA, MASANORI;PAUWELS, RUDI;VAN, AERSCHOT+, J. MED. CHEM., 31,(1988) N 10, C. 2040-2048
  作者：HERDEWIJN, PIET、BALZARINI, JAN、BADA, MASANORI、PAUWELS, RUDI、VAN, AERSCHOT+

  DOI：——

  日期：——
• Synthesis and anti-HIV activity of different sugar-modified pyrimidine and purine nucleosides
  作者：Piet Herdewijn、Jan Balzarini、Masanori Baba、Rudi Pauwels、Arthur Van Aerschot、Gerard Janssen、Erik De Clercq

  DOI：10.1021/jm00118a033

  日期：1988.10

  A series of base-modified pyrimidine 3'-azido-2',3'-dideoxynucleosides and 3'-substituted purine and pyrimidine 2',3'-dideoxynucleosides have been synthesized and evaluated for their inhibitory activity against human immunodeficiency virus (HIV) replication in MT-4 cells. The following pyrimidine derivatives emerged as the most potent and/or selective inhibitors of HIV-induced cytopathogenicity (in order of decreasing selectivity: 3'-azido-3'-deoxythymidine (AZT), 3'-azido-2',3'-dideoxyuridine (AzddUrd), 3'-azido-2',3'-dideoxy-5-methylcytidine (AzddMeCyd), 3'-fluoro-ddUrd (FddUrd), 3'-fluoro-ddThd (FddThd), the N4-hydroxylated derivative of AzddMeCyd and the N4-methylated derivative of AzddMeCyd. Among the purine 2',3'-dideoxynucleosides, 3'-azido-2',3'-dideoxyguanosine (AzddGuo), 3'-fluoro-ddGuo (FddGuo), and 3'-fluoro-2,6-diaminopurine 2',3'-dideoxynucleoside (FddDAPR) were the most selective inhibitors of HIV replication.