(2R)-5-甲氧基-1,3-恶噻戊环-2-甲醇2-苯甲酸酯 | 528567-33-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: (2R)-5-甲氧基-1,3-恶噻戊环-2-甲醇2-苯甲酸酯
• 英文名称: 5-methoxy-2-benzoyloxymethyl[1,3]oxathiolane
• 英文别名: (2R)-5-methoxy-1,3-oxathiolane-2-methyl benzoate；(2R)-5-Methoxy-1,3-oxathiolane-2-methanol 2-Benzoate；[(2R)-5-methoxy-1,3-oxathiolan-2-yl]methyl benzoate
• CAS: 528567-33-1
• 化学式: C₁₂H₁₄O₄S
• 分子量: 254.307
• InChiKey: SMKDHPIQHWRJFP-RRKGBCIJSA-N

物化性质

• 沸点：
  379.3±42.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)
• 溶解度：
  溶于氯仿

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  70.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  bis-TMS-N-acetylcytosine 、 (2R)-5-甲氧基-1,3-恶噻戊环-2-甲醇2-苯甲酸酯 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以60%的产率得到((2R,5S)-5-(4-acetamido-2-oxopyrimidin-1(2H)-yl)-1,3-oxathiolan-2-yl)methyl benzoate
  参考文献：
  名称：

  A PROCESS FOR STEREOSELECTIVE SYNTHESIS OF LAMIVUDINE

  摘要：

  公开号：

  EP2161267B1
• 作为产物：
  描述：

  menthyl 5-hydroxy[1,3]oxathiolane-2-carboxylate 在 吡啶 、 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 (2R)-5-甲氧基-1,3-恶噻戊环-2-甲醇2-苯甲酸酯
  参考文献：
  名称：

  Synthesis of oxathiolane imidazole nucleosides

  摘要：

  Nucleosides have been of great interest since their strong antiviral activities were discovered. 1,3-Oxathiolane ring system has been known for many years, but it is in recent years that the ring has been used as the sugar ring in nucleoside analogs (Synthesis (1991) 1046; J. Am. Chem. Soc. 113 (1991) 9377; Tetrahedron Lett. 35 (1994) 4739). Besides, bredinin is a natural nucleoside antibiotic with imidazole moiety and there are some other studies reported on nucleosides with the imidazole group (Biorg. Med. Chem. 7 (1999) 48 1; Biorg. Med. Chem. 7 (1999) 1617; Nucleosides Nucleotides 18 (1099) 3 3 1). These findings make the imidazole group interesting as the base of a nucleoside. In this study, in order to find out the structure-activity relationships Of L-oxathiolanyl nucleosides, L-oxathiolanyl imidazole nucleosides 7 and 8 were synthesized, via novel intermediates 2-6, which were then tested for anti-HIV activity (Antivir. Res. 1-11 (1994) 25) in human peripheral blood mononuclear (PBM) cells, the synthesized nucleosides did not show significant activity up to 100 muM against HIV-1. (C) 2002 Editions scientifiques et medicales Elsevier SAS. All rights reserved.

  DOI：

  10.1016/s0014-827x(02)01287-9

文献信息

• Synthesis of oxathiolane imidazole nucleosides
  作者：Ayse Kocabalkanli、Raymond F Schinazi

  DOI：10.1016/s0014-827x(02)01287-9

  日期：2002.12

  Nucleosides have been of great interest since their strong antiviral activities were discovered. 1,3-Oxathiolane ring system has been known for many years, but it is in recent years that the ring has been used as the sugar ring in nucleoside analogs (Synthesis (1991) 1046; J. Am. Chem. Soc. 113 (1991) 9377; Tetrahedron Lett. 35 (1994) 4739). Besides, bredinin is a natural nucleoside antibiotic with imidazole moiety and there are some other studies reported on nucleosides with the imidazole group (Biorg. Med. Chem. 7 (1999) 48 1; Biorg. Med. Chem. 7 (1999) 1617; Nucleosides Nucleotides 18 (1099) 3 3 1). These findings make the imidazole group interesting as the base of a nucleoside. In this study, in order to find out the structure-activity relationships Of L-oxathiolanyl nucleosides, L-oxathiolanyl imidazole nucleosides 7 and 8 were synthesized, via novel intermediates 2-6, which were then tested for anti-HIV activity (Antivir. Res. 1-11 (1994) 25) in human peripheral blood mononuclear (PBM) cells, the synthesized nucleosides did not show significant activity up to 100 muM against HIV-1. (C) 2002 Editions scientifiques et medicales Elsevier SAS. All rights reserved.
• A PROCESS FOR STEREOSELECTIVE SYNTHESIS OF LAMIVUDINE
  申请人：Shanghai Desano Pharmaceutical Holding Co., Ltd.

  公开号：EP2161267B1

  公开（公告）日：2014-04-30