(1R,4R,5S)-4-tert-butyldimethylsilyloxymethyl-5-tert-butyldimethylsilyloxycyclohex-2-en-1-ol | 247587-58-2

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (1R,4R,5S)-4-tert-butyldimethylsilyloxymethyl-5-tert-butyldimethylsilyloxycyclohex-2-en-1-ol
• 英文别名: (1R,4R,5S)-5-(tert-butyldimethylsilyloxy)-4-(tert-butyldimethylsilyloxymethyl)-cyclohex-2-en-1-ol；(1R,4R,5S)-5-[tert-butyl(dimethyl)silyl]oxy-4-[[tert-butyl(dimethyl)silyl]oxymethyl]cyclohex-2-en-1-ol
• CAS: 247587-58-2
• 化学式: C₁₉H₄₀O₃Si₂
• 分子量: 372.696
• InChiKey: OWOFSMVXUNYERA-IKGGRYGDSA-N

物化性质

• 沸点：
  379.8±42.0 °C(Predicted)
• 密度：
  0.93±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.34
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1R,4R,5S)-4-tert-butyldimethylsilyloxymethyl-5-tert-butyldimethylsilyloxycyclohex-2-en-1-ol 在 三苯基膦 、 三氟乙酸 、 偶氮二甲酸二乙酯 作用下， 以 1,4-二氧六环 、 水 为溶剂， 生成 D-cyclohexenyl G
  参考文献：
  名称：

  （D）-和（L）-环己烯醇-G，一类新的抗病毒剂：合成，构象分析，分子建模和生物活性

  摘要：

  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。

  DOI：

  10.1081/ncn-100002360
• 作为产物：
  描述：

  (1R,2S,3S,5R)-5-benzyloxy-3-(tert-butyldimethylsilyloxy)-2-hydroxymethyl-cyclohexanol 在 palladium on activated charcoal 咪唑 、 manganese(IV) oxide 、 sodium tetrahydroborate 、 cerium(III) chloride 、 甲酸铵 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 生成 (1R,4R,5S)-4-tert-butyldimethylsilyloxymethyl-5-tert-butyldimethylsilyloxycyclohex-2-en-1-ol
  参考文献：
  名称：

  Enantioselective Synthesis and Conformational Analysis of Cyclohexene Carbocyclic Nucleosides

  摘要：

  An enantioselective approach towards the synthesis of optically pure cyclohexene nucleosides 3 has been developed starting from (R)-carvone. The key steps are the regio- and stereoselective hydroboration of an exo double bond, the selective reduction of an enone intermediate and introduction of a base moiety by Mitsunobu reaction. Conformational analysis showed that the adenine base adopts predominantly in a pseudo-axial position.

  DOI：

  10.1080/15257779908041505

文献信息

• Compounds and oligomeric compounds comprising novel nucleobases
  申请人：——

  公开号：US20040033973A1

  公开（公告）日：2004-02-19

  The present invention relates to nucleoside compositions comprising novel nucleobases and oligomeric compounds comprising at least one such nucleoside. These oligomeric compounds typically have enhanced binding affinity properties compared to oligomeric compounds without the modification. The oligomeric compounds are useful, for example, for investigative and therapeutic purposes.

  本发明涉及包含新型核碱基的核苷酸组合物以及包含至少一种此类核苷酸的寡聚合物化合物。这些寡聚合物化合物通常具有比没有这种修饰的寡聚合物化合物更强的结合亲和性能。这些寡聚合物化合物可用于调查和治疗等用途。
• CARBOCYCLIC NUCLEOSIDES AND PROCESS FOR OBTAINING SUCH
  申请人：Stichting REGA V.Z.W.

  公开号：EP1210347B1

  公开（公告）日：2004-06-23
• 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.
• The Cyclohexene Ring System as a Furanose Mimic:  Synthesis and Antiviral Activity of Both Enantiomers of Cyclohexenylguanine
  作者：Jing Wang、Matheus Froeyen、Chris Hendrix、Graciela Andrei、Robert Snoeck、Erik De Clercq、Piet Herdewijn

  DOI：10.1021/jm991171l

  日期：2000.2.1

  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.