(1R,2S,3S,5S)-5-benzyloxy-3-(tert-butyldimethylsilyloxy)-2-(tert-butyldimethylsilyloxymethyl)-1-methanesulfonyloxycyclohexane | 247587-55-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (1R,2S,3S,5S)-5-benzyloxy-3-(tert-butyldimethylsilyloxy)-2-(tert-butyldimethylsilyloxymethyl)-1-methanesulfonyloxycyclohexane
• 英文别名: (1R,2R,3S,5S)-5-benzyloxy-2-(tertbutyldimethylsilyloxymethyl)-3-(tert-butyldimethylsilyoxy)-1-methanesulfonyloxy-cyclohexane；(1R,2R,3S,5S)-5-Benzyloxy-2-(tert-butyldimethylsilyloxymethyl)-3-(tert-butyldimethylsilyoxy)-1-methanesulfonyloxy-cyclohexane；[(1R,2R,3S,5S)-3-[tert-butyl(dimethyl)silyl]oxy-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-5-phenylmethoxycyclohexyl] methanesulfonate
• CAS: 247587-55-9
• 化学式: C₂₇H₅₀O₆SSi₂
• 分子量: 558.927
• InChiKey: RTFJZBLGAROONK-RCTAOEEJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.74
• 重原子数：
  36
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  79.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (1R,2S,3S,5S)-5-benzyloxy-3-(tert-butyldimethylsilyloxy)-2-(tert-butyldimethylsilyloxymethyl)-1-methanesulfonyloxycyclohexane 在 palladium on activated charcoal manganese(IV) oxide 、 sodium tetrahydroborate 、 cerium(III) chloride 、 甲酸铵 作用下， 以 甲醇 、 二氯甲烷 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：

  （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 咪唑 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 (1R,2S,3S,5S)-5-benzyloxy-3-(tert-butyldimethylsilyloxy)-2-(tert-butyldimethylsilyloxymethyl)-1-methanesulfonyloxycyclohexane
  参考文献：
  名称：

  Enantioselective Synthesis and Conformational Study of Cyclohexene Carbocyclic Nucleosides

  摘要：

  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.

  DOI：

  10.1021/jo9908288

文献信息

• 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 Analysis of Cyclohexene Carbocyclic Nucleosides
  作者：Jing Wang、Piet Herdewijn

  DOI：10.1080/15257779908041505

  日期：1999.4

  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.