甲磺酸,三氟-,(1S,2S,3S)-2,3-二[(苯甲酰氧基)甲基]环丁基酯 | 163928-93-6

• 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: 甲磺酸,三氟-,(1S,2S,3S)-2,3-二[(苯甲酰氧基)甲基]环丁基酯
• 英文名称: [(1S,2S,3S)-2-(benzoyloxymethyl)-3-(trifluoromethylsulfonyloxy)cyclobutyl]methyl benzoate
• CAS: 163928-93-6
• 化学式: C₂₁H₁₉F₃O₇S
• 分子量: 472.439
• InChiKey: ZPLIHWACAWHWGD-KURKYZTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  32
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  104
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  甲磺酸,三氟-,(1S,2S,3S)-2,3-二[(苯甲酰氧基)甲基]环丁基酯 在 劳森试剂 、 吡啶 、 盐酸 、 甲酸 作用下， 以 1,4-二氧六环 、 六甲基磷酰三胺 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 生成
  参考文献：
  名称：

  Synthesis of C-oxetanosyl-thiazole and its carbocyclic analog nucleosides as potential chemotherapeutic agents

  摘要：

  Novel C-nucleosides (2'S, 3'S)-2-[2', 3'-(bishydroxymethyl)-oxetan-1'-yl]-1,3-thiazole-4-carboxamide 3 and its carbocyclic analog 4 have been synthesized. Compound 4 enhanced NGF-induced differentiation on PC12 cells at 100 mu g/ml, and moreover, 4 alone also induced morphological differentiation significantly at 10 and 100 mu g/ml. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0960-894x(96)00340-x
• 作为产物：
  描述：

  三氟甲磺酸酐 、 (1S,2S,3S)-2,3-二(苯甲酰基氧基甲基)环丁醇 在 吡啶 作用下， 生成 甲磺酸,三氟-,(1S,2S,3S)-2,3-二[(苯甲酰氧基)甲基]环丁基酯
  参考文献：
  名称：

  Expedient Approach to Chiral Cyclobutanones:  Asymmetric Synthesis of Cyclobut-G

  摘要：

  An efficient one-pot asymmetric synthesis of cyclobutanones from chiral enol ethers is described. The approach is illustrated with alkyl- and functionalized alkyl-substituted enol ethers (nine examples). A new enantioselective synthesis of cyclobut-G (Lobucavir) could thus be achieved.

  DOI：

  10.1021/ol702977x

文献信息

• A Practical Asymmetric Synthesis of the Antiviral Agent Lobucavir, BMS-180194
  作者：Janak Singh、Gregory S. Bisacchi、Saleem Ahmad、Jollie D. Godfrey,、Thomas P. Kissick、Toomas Mitt、Octavian Kocy、Truc Vu、Chris G. Papaioannou、Michael K. Wong、James E. Heikes、Robert Zahler、Richard H. Mueller

  DOI：10.1021/op970214+

  日期：1998.11.1

  A practical synthesis of the antiviral agent lobucavir, [1R(1 alpha,2 beta,3 alpha)] -2-amino-9-[2,3-bis(hydroxymethyl)cyclobutyl]-6H-purin-6-one (BMS-180194), is described. The key chiral intermediate, [1S-(1 alpha,2 beta,3 alpha)]-3-hydroxy-1,2-cyclobutanedimethanol, dihenzoate ester, was made by an asymmetric [2 + 2] cycloaddition of dimenthyl fumarate with ketene dimethyl acetal followed by sequential diester reduction, benzoylation, deketalization, and stereoselective ketone reduction. Regioselective N9-alkylation of the tetra-n-butylammonium salt of 2-amino-6-iodopurine with the derived cyclobutyltriflate furnished the purinecyclobutyl dibenzoate. Methanolysis followed by acid hydrolysis produced lobucavir in a 35% overall yield with an ee, 99%.
• Expedient Approach to Chiral Cyclobutanones:  Asymmetric Synthesis of Cyclobut-G
  作者：Benjamin Darses、Andrew E. Greene、Susannah C. Coote、Jean-François Poisson

  DOI：10.1021/ol702977x

  日期：2008.3.1

  An efficient one-pot asymmetric synthesis of cyclobutanones from chiral enol ethers is described. The approach is illustrated with alkyl- and functionalized alkyl-substituted enol ethers (nine examples). A new enantioselective synthesis of cyclobut-G (Lobucavir) could thus be achieved.
• Synthesis of C-oxetanosyl-thiazole and its carbocyclic analog nucleosides as potential chemotherapeutic agents
  作者：Yoshiko Kikuchi、Shigeru Nishiyama、Shosuke Yamamura、Kuniki Kato、Sari Fujiwara、Kazuo Umezawa、Yukimasa Terada

  DOI：10.1016/0960-894x(96)00340-x

  日期：1996.8

  Novel C-nucleosides (2'S, 3'S)-2-[2', 3'-(bishydroxymethyl)-oxetan-1'-yl]-1,3-thiazole-4-carboxamide 3 and its carbocyclic analog 4 have been synthesized. Compound 4 enhanced NGF-induced differentiation on PC12 cells at 100 mu g/ml, and moreover, 4 alone also induced morphological differentiation significantly at 10 and 100 mu g/ml. Copyright (C) 1996 Elsevier Science Ltd