(1R,2S,3S,5R)-5-benzyloxy-3-(tert-butyldimethylsilyloxy)-2-hydroxymethyl-cyclohexanol | 247587-52-6

• 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,5R)-5-benzyloxy-3-(tert-butyldimethylsilyloxy)-2-hydroxymethyl-cyclohexanol
• 英文别名: (1R,2S,3S,5R)-3-[tert-butyl(dimethyl)silyl]oxy-2-(hydroxymethyl)-5-phenylmethoxycyclohexan-1-ol
• CAS: 247587-52-6
• 化学式: C₂₀H₃₄O₄Si
• 分子量: 366.573
• InChiKey: ODWHSRJGAVCLHD-HCXYKTFWSA-N

物化性质

• 沸点：
  444.8±45.0 °C(Predicted)
• 密度：
  1.05±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.73
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 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)-5-benzyloxy-3-(tert-butyldimethylsilyloxy)-2-hydroxymethyl-cyclohexanol 在 palladium on activated charcoal 咪唑 、 甲酸铵 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 15.0h， 生成 (1R,3R,4R,5S)-4-tert-butyldimethylsilyloxymethyl-5-tert-butyldimethylsilyloxy-3-methanesulfonyloxycyclohexanol
  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
• 作为产物：
  描述：

  ((1R,2S,4R,6R)-4-Benzyloxy-1-methyl-7-oxa-bicyclo[4.1.0]hept-2-yloxy)-tert-butyl-dimethyl-silane 在 9-borabicyclo[3.3.1]nonane dimer 、 2,2,6,6-tetramethylpiperidinyl-lithium 、 氯化二乙基铝 作用下， 以 四氢呋喃 、 甲苯 、 苯 为溶剂， 反应 54.0h， 生成 (1R,2S,3S,5R)-5-benzyloxy-3-(tert-butyldimethylsilyloxy)-2-hydroxymethyl-cyclohexanol
  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.