1,2-环丁二甲醇,3-(2-氨基-6-碘-9H-嘌呤-9-基)-,二苯酸酯(ester),(1S,2R,3R)- | 156126-83-9

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 核苷和核苷酸类似物
• 中文名称: 1,2-环丁二甲醇,3-(2-氨基-6-碘-9H-嘌呤-9-基)-,二苯酸酯(ester),(1S,2R,3R)-
• 英文名称: <1S-(1α,2β,3α)>-3-(2-Amino-6-iodo-9H-purin-9-yl)-1,2-cyclobutanedimethanol dibenzoate ester
• 英文别名: [1S-(1α,2β,3α)]-3-(2-Amino-6-iodo-9H-purin-9-yl)-1,2-cyclobutanedimethanol. dibenzoate ester；(1S-(1α,2β,3α))-3-(2-Amino-6-iodo-9H-purin-9-yl)-1,2-cyclobutanedimethanol dibenzoate ester；[(1S,2R,3R)-3-(2-amino-6-iodopurin-9-yl)-2-(benzoyloxymethyl)cyclobutyl]methyl benzoate
• CAS: 156126-83-9
• 化学式: C₂₅H₂₂IN₅O₄
• 分子量: 583.385
• InChiKey: GKXWRKUZBGXUMV-GUDVDZBRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  35
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  122
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1,2-环丁二甲醇,3-(2-氨基-6-碘-9H-嘌呤-9-基)-,二苯酸酯(ester),(1S,2R,3R)- 在 溶剂黄146 作用下， 以77%的产率得到[(1S,2R,3R)-3-(2-amino-6-oxo-1H-purin-9-yl)-2-(benzoyloxymethyl)cyclobutyl]methyl benzoate
  参考文献：
  名称：

  Regioselective Coupling of Tetraalkylammonium Salts of 6-Iodo-2-aminopurine to a Cyclobutyl Triflate: Efficient Preparation of Homochiral BMS-180,194, a Potent Antiviral Carbocyclic Nucleoside

  摘要：

  DOI：

  10.1021/jo00114a047
• 作为产物：
  描述：

  、 甲磺酸,三氟-,(1S,2S,3S)-2,3-二[(苯甲酰氧基)甲基]环丁基酯 生成 1,2-环丁二甲醇,3-(2-氨基-6-碘-9H-嘌呤-9-基)-,二苯酸酯(ester),(1S,2R,3R)-
  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%.