(1R,2S,3S,5R)-3,5-bis[[tert-butyl(dimethyl)silyl]oxy]-2-(hydroxymethyl)cyclohexan-1-ol | 262372-05-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1R,2S,3S,5R)-3,5-bis[[tert-butyl(dimethyl)silyl]oxy]-2-(hydroxymethyl)cyclohexan-1-ol
• CAS: 262372-05-4
• 化学式: C₁₉H₄₂O₄Si₂
• 分子量: 390.711
• InChiKey: HPQNFRZAFJUXKD-TWMKSMIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.53
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1R,2S,3S,5R)-3,5-bis[[tert-butyl(dimethyl)silyl]oxy]-2-(hydroxymethyl)cyclohexan-1-ol 在 4-二甲氨基吡啶 、 重铬酸吡啶 、 四丁基氟化铵 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 34.5h， 生成 (4S,5R)-5-benzoyl-4-benzoylmethylcyclohex-2-en-1-one
  参考文献：
  名称：

  The Cyclohexene Ring System as a Furanose Mimic:  Synthesis and Antiviral Activity of Both Enantiomers of Cyclohexenylguanine

  摘要：

  Both enantiomers of cyclohexenylguanine were synthesized in a stereospecific way starting from the same starting material: R-(-)-carvone. Both compounds showed potent-and selective anti-herpesvirus activity (HSV-1, HSV-2, VZV, CMV). The binding of both cyclohexene nucleosides in the active site of HSV-1 thymidine kinase was investigated, and a model for the binding of both enantiomers is proposed. The amino acids involved in binding of the optical antipodes are the same, but the interaction energy of both enantiomers is slightly different. This may be attributed to the interaction of the secondary hydroxyl function of the nucleoside analogues with Glu-225. Structural analysis has demonstrated the flexibility of the cyclohexenyl system, and this may be considered as an important conformational characteristic explaining the potent antiviral activity.

  DOI：

  10.1021/jm991171l
• 作为产物：
  描述：

  (R)-Carvone 生成 (1R,2S,3S,5R)-3,5-bis[[tert-butyl(dimethyl)silyl]oxy]-2-(hydroxymethyl)cyclohexan-1-ol
  参考文献：
  名称：

  CARBOCYCLIC NUCLEOSIDES AND PROCESS FOR OBTAINING SUCH

  摘要：

  公开号：

  EP1210347B1

文献信息

• (D)- AND (L)-CYCLOHEXENYL-G, A NEW CLASS OF ANTIVIRAL AGENTS: SYNTHESIS, CONFORMATIONAL ANALYSIS, MOLECULAR MODELING, AND BIOLOGICAL ACTIVITY
  作者：J. Wang、M. Froeyen、C. Hendrix、C. Andrei、R. Snoeck、E. Lescrinier、E. De Clercq、P. Herdewijn

  DOI：10.1081/ncn-100002360

  日期：2001.3.31

  (D)- and (L)-cyclohexeneyl-G were synthesized enantioselectively starting from (R)-carvone. Both show potent and selective anti-herpesvirus activity (HSV-1, HSV-2, VZV, CMV). Molecular modeling demonstrates that both isomers are bound in the active site of HSV-1 thymidine kinase in a high-energy conformation with the base moiety orienting in an equatorial position. It is believed that the flexibility

  从（R）-香芹酮开始对映选择性地合成（D）-和（L）-环己烯基-G。两者均显示有效和选择性的抗疱疹病毒活性（HSV-1，HSV-2，VZV，CMV）。分子建模表明，两种异构体均以高能构象结合在HSV-1胸苷激酶的活性位点上，且碱基部分位于赤道位置。据信，环己烯环的柔韧性对其抗病毒活性至关重要。
• Enantioselective Synthesis and Conformational Study of Cyclohexene Carbocyclic Nucleosides
  作者：Jing Wang、Piet Herdewijn

  DOI：10.1021/jo9908288

  日期：1999.10.1

  Enantioselective synthesis of a new family of unsaturated six-membered carbocyclic nucleosides using (R)-(-)-can one as starting material is described. Introduction of the base moiety via Mitsunobu reaction proceeded regio- and stereoselectively and with good chemical yield, while the Pd-coupling approach failed. H-1 NMR study and molecular modeling show the adenine compound exists in an equilibrium of H-3(2) and H-2(3) conformers (ratio 7:3) in favor of the 3'-endo half-chair conformation, with the base oriented in a pseudoaxial position. This conformational preference can be explained by the pi --> sigma*(C1')-(N1) interaction involving the antibonding orbital of the C1'-N bond.