1-O-acetyl-2-deoxy-3,5-di-O-toluoyl-4-thio-D-ribofuranose | 169736-17-8

• 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: 1-O-acetyl-2-deoxy-3,5-di-O-toluoyl-4-thio-D-ribofuranose
• 英文别名: 1-O-acetyl-3,5-di-O-p-toluoyl-4-thio-D-erythropentofuranose；1-O-acetyl-2-deoxy-4-thio-3,5-di-O-p-toluoyl-D-erythro-pentofuranose；1-O-acetyl-2-deoxy-4-thio-3,5-di-O-p-toluoyl-4-thio-D-erythro-pentofuranose；[(2R,3S)-5-acetyloxy-3-(4-methylbenzoyl)oxythiolan-2-yl]methyl 4-methylbenzoate
• CAS: 169736-17-8
• 化学式: C₂₃H₂₄O₆S
• 分子量: 428.506
• InChiKey: BTWDIWFRMOGOBD-MCOCGALXSA-N

物化性质

• 沸点：
  556.2±50.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  30
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  104
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-O-acetyl-2-deoxy-3,5-di-O-toluoyl-4-thio-D-ribofuranose 在 三甲基氯硅烷 、 三氟甲磺酸三甲基硅酯 、 sodium methylate 、 六甲基二硅氮烷 作用下， 以 甲醇 为溶剂， 反应 5.0h， 生成 4-氨基-1-[(4S,5R)-4-羟基-5-(羟基甲基)四氢噻吩-2-基]嘧啶-2-酮
  参考文献：
  名称：

  Synthesis and biological activity of 2'-deoxy-4'-thio pyrimidine nucleosides

  摘要：

  2'-Deoxy-4'-thiocytidine (7-beta), 2'-deoxy-4'-thiouridine (9), and 4'-thiothymidine (10) have been synthesized and evaluated for cytotoxicity in vitro. All these compounds were cytotoxic to L1210, H-Ep-2, and CCRF-CEM cell lines. 4'-Thiothymidine was also active against herpes simplex 1 and human cytomegalovirus in cell culture.

  DOI：

  10.1021/jm00112a007
• 作为产物：
  描述：

  benzyl 3,5-di-O-benzyl-2-deoxy-1,4-dithio-D-erythro-pentofuranoside 在 吡啶 、 三氯化硼 作用下， 以 二氯甲烷 、 溶剂黄146 为溶剂， 反应 4.5h， 生成 1-O-acetyl-2-deoxy-3,5-di-O-toluoyl-4-thio-D-ribofuranose
  参考文献：
  名称：

  Synthesis and Anti-Herpes Virus Activity of 2‘-Deoxy-4‘-thiopyrimidine Nucleosides

  摘要：

  A series of 5-substituted 2'-deoxy-4'-thiopyrimidine nucleosides was synthesized and evaluated as potential antiviral agents. A number of analogues such as 2'-deoxy-5-propyl-4'-thiouridine (3ii), 2'-deoxy-5-isopropyl-4'-thiouridine (3iii), 5-cyclopropyl-2'-deoxy-4'-thiouridine (3iv), 2'-deoxy-4'-thio-5-vinyluridine (3viii), and 5-(2-chloroethyl)-2'-deoxy-4'-thiouridin (3xx) were found to be highly active against herpes simplex virus type-1 (HSV-1) and varicella tester virus (VZV) in vitro with no significant cytotoxicity. The compound with the broadest spectrum of activity was 2'-deoxy-5-ethyl-4'-thiouridine (3i) which showed significant activity against HSV-1, HSV-2, and VZV.

  DOI：

  10.1021/jm950029r

文献信息

• Synthesis and Anti-cancer Activity of Some Novel 5-Azacytosine Nucleosides
  作者：Kamal N. Tiwari、Loredana Cappellacci、John A. Montgomery、John A. Secrist III

  DOI：10.1081/ncn-120026872

  日期：2003.12.31

  1-O-Acetyl-2-deoxy-3,5-di-O-toluoyl-4-thio-D-erythro-pentofuranose and 2-deoxy-1,3,5-tri-O-acetyl-4-thio-L-threo-pentofuranose were coupled with 5-azacytosine to obtain alpha and beta anomers of nucleosides. All four nucleosides were reduced to the corresponding dihydro derivatives and deblocked to give target compounds. All eight target compounds were evaluated in a series of human cancer cell lines

  1-O-乙酰基-2-脱氧-3,5-二-O-甲苯基-4-硫代-D-赤型戊呋喃糖和2-脱氧-1,3,5-三-O-乙酰基-4-硫代-将L-苏-戊呋喃糖与5-氮杂胞嘧啶偶联以获得核苷的α和β异构体。将所有四个核苷还原为相应的二氢衍生物，并解封以得到目标化合物。在培养的一系列人类癌细胞系中评估了所有八个目标化合物。发现仅2'-脱氧-4'-硫代-5-氮杂胞苷（3beta）在所有细胞系中均具有细胞毒性，并在体内进行了进一步评估。报告了合成和生物活性的细节。
• SYNTHESIS AND BIOLOGICAL ACTIVITY OF 2′-DEOXY-4′-THIO-PYRAZOLO[3,4-<i>d</i>]PYRIMIDINE NUCLEOSIDES
  作者：K. N. Tiwari、A. S. Fowler、J. A. Secrist

  DOI：10.1081/ncn-200059266

  日期：2005.4.1

  4-aminopyrazolo [3, 4-d]pyrimidine with the appropriate thio sugar gave a 3:1 ratio of α,β blocked 4-amino-1-(2-deoxy-4-thio-D-erythropentofuranosyl)- 1H pyrazolo[3,4-d]pyrimidine nucleosides. The mixture was deblocked, both the anomers were separated, and the β-anomer was readily deaminated by adenosine deaminase. The nucleosides have been characterized, and their anomeric configurations have been determined

  4-氨基吡唑并 [3, 4-d] 嘧啶与合适的硫糖的偶联得到 3:1 比例的 α,β 封闭 4-氨基-1-(2-脱氧-4-硫代-D-呋喃红糖基)- 1H 吡唑并[3,4-d]嘧啶核苷。混合物被解封，两种异头物被分离，β-异头物很容易被腺苷脱氨酶脱氨基。核苷已被表征，它们的异头构型已通过质子核磁共振确定。针对一组人肿瘤细胞系在体外评估了所有三种核苷的细胞毒性。描述了这些核苷的方便和高产合成的细节。
• Synthesis and Biological Activity of 5-Azacytosine Nucleosides Derived from 4-Thio-2-Deoxy-L-<i>threo</i>-Pentofuranose and 4-Thio-2-Deoxy-D-<i>erythro</i>-Pentofuranose
  作者：Loredana Cappellacci、Kamal N. Tiwari、John A. Montgomery、John A. Secrist

  DOI：10.1080/15257779908041514

  日期：1999.4

  1-O-Acetyl-2-deoxy-3,5-di-O-toluoyl-4-thio-D-erythro-pentofuranose and and 2-deoxy-1,3,5-tri-O-acetyl-4-thio-L-threo-pentofuranose were coupled with 5-azacytosine to obtain alpha and beta anomers of nucleosides.
• Synthesis and Biological Activity of 4′-Thio-2′-deoxy Purine Nucleosides
  作者：Lea Messini、Kamal N. Tiwari、John A. Montgomery、John A. Secrist

  DOI：10.1080/15257779908041540

  日期：1999.4

  Coupling of 1-O-acetyl-2-deoxy-3,5-di-O-toluoyl-4-thio-D-ribofuranose with 6-chloropurine and 2,6-dichloropurine gave a mixture of 9 alpha and 9 beta anomers as major products. These anomers were separated and converted to 2'-deoxy-4'-thio analogues of adenosine, inosine, guanosine, 2-amino-adenosine, and 2-chloro adenosine as well as their alpha-anomers.
• Basnak; Otter; Duncombe, Nucleosides and Nucleotides, 1998, vol. 17, # 1-3, p. 29 - 38
  作者：Basnak、Otter、Duncombe、Westwood、Pietrarelli、Hardy、Mills、Rahim、Walker

  DOI：——

  日期：——