(1S,2R)-2-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]cyclopropane-1-carboxylic acid | 158262-94-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S,2R)-2-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]cyclopropane-1-carboxylic acid
• CAS: 158262-94-3
• 化学式: C₉H₁₄O₄
• 分子量: 186.208
• InChiKey: MAXDZRDHHPTSEH-DSYKOEDSSA-N

物化性质

• 沸点：
  295.7±35.0 °C(predicted)
• 密度：
  1.255±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1S,2R)-2-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]cyclopropane-1-carboxylic acid 在 palladium on activated charcoal sodium azide 、 氢气 、 sodium methylate 、 三乙胺 、 2-巯基乙醇 作用下， 以 1,4-二氧六环 、 甲醇 、 丙酮 、 甲苯 为溶剂， 120.0 ℃ 、206.84 kPa 条件下， 反应 29.5h， 生成 (1'S,2'R,4''S)-9-<2-(2,2-Dimethyl-1,3-dioxolan-4-yl)cyclopropyl>hypoxanthine
  参考文献：
  名称：

  Asymmetric Synthesis of (1'S,2'R)-Cyclopropyl Carbocyclic Nucleosides

  摘要：

  Enantiomeric synthesis of cyclopropyl carbocyclic nucleosides has been accomplished. The key intermediates 7 and 9 were synthesized from D-glyceraldehyde acetonide 1, which was converted to the alpha,beta-unsaturated ester 2 and then reduced to give allylic alcohol 3a. Stereoselective construction of the cyclopropyl ring of 3a and 3b followed by oxidation gave acid 5, which was treated under Curtius rearrangement conditions to obtain the urea intermediate 7. The urea intermediate was utilized to prepare uracil 14, thymine 15, and cytosine 18 nucleosides. The purine derivatives were prepared from cyclopropylamine 9 by condensation with 4,6-dichloro-5-form-amidopyrimidine or 4,6-dichloro-2-aminopyrimidine.

  DOI：

  10.1021/jo00121a047
• 作为产物：
  描述：

  双丙酮-D-甘露糖醇 在 ruthenium(IV) oxide 咪唑 、 lead(IV) acetate 、 sodium periodate 、 四丁基氟化铵 、 diethylzinc 、 二异丁基氢化铝 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 、 氯仿 、 水 、 乙酸乙酯 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 21.83h， 生成 (1S,2R)-2-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]cyclopropane-1-carboxylic acid
  参考文献：
  名称：

  Asymmetric Synthesis of (1'S,2'R)-Cyclopropyl Carbocyclic Nucleosides

  摘要：

  Enantiomeric synthesis of cyclopropyl carbocyclic nucleosides has been accomplished. The key intermediates 7 and 9 were synthesized from D-glyceraldehyde acetonide 1, which was converted to the alpha,beta-unsaturated ester 2 and then reduced to give allylic alcohol 3a. Stereoselective construction of the cyclopropyl ring of 3a and 3b followed by oxidation gave acid 5, which was treated under Curtius rearrangement conditions to obtain the urea intermediate 7. The urea intermediate was utilized to prepare uracil 14, thymine 15, and cytosine 18 nucleosides. The purine derivatives were prepared from cyclopropylamine 9 by condensation with 4,6-dichloro-5-form-amidopyrimidine or 4,6-dichloro-2-aminopyrimidine.

  DOI：

  10.1021/jo00121a047

文献信息

• Synthesis of enantiomerically pure cyclopropyl carbocyclic nucleosides
  作者：Yufen Zhao、Te-Fang Yang、Migyoung Lee、Byoung K. Chun、Jinfa Du、Raymond F. Schinazi、Doowon Lee、M.Gary Newton、Chung K. Chu

  DOI：10.1016/s0040-4039(00)73511-8

  日期：1994.7

  The enantiomeric synthesis of cyclopropyl carbocyclic nucleosides has been achieved and the key intermediate was characterized by X-ray crystallography.

  已经实现了环丙基碳环核苷的对映体合成，并且通过X射线晶体学表征了关键中间体。
• Asymmetric Synthesis of Cyclopropyl Carbocyclic Nucleosides
  作者：Y. F. Zhao、M. G. Lee、T. -F. Yang、B. K. Chun、J. F. Du、R. F. Schinazi、C. K. Chu

  DOI：10.1080/15257779508012367

  日期：1995.5.1

  Abstract A number of nucleosides have been synthesized as potential antiviral and antitumor agents.1 More recently, various dideoxynucleosides have been synthesized and found to be potent anti-HIV agents.2 As a part of our drug discovery program for the treatment of HIV and HBV, we have initiated to synthesize cyclopropyl carbocyclic nucleosides as potential antiviral agents. Several papers regarding

  摘要已合成了许多核苷作为潜在的抗病毒药和抗肿瘤药。1最近，已合成了多种双脱氧核苷，发现它们是有效的抗HIV药物。2作为我们用于治疗HIV和HBV的药物发现计划的一部分，我们已经开始合成环丙基碳环核苷作为潜在的抗病毒剂。关于环丙基碳环核苷合成的几篇论文已经出现在文献中。3-5然而，它们都被报告为外消旋混合物。在此摘要中，我们希望报告由旋光性常用中间体6和11不对称合成环丙基碳环核苷的方法。