(1R,2S,3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-cyclohexanol | 328926-58-5

• 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-silanyloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-cyclohexanol
• 英文别名: (1R,2S,3S,5R)-3,5-bis[[tert-butyl(dimethyl)silyl]oxy]-2-[[tert-butyl(dimethyl)silyl]oxymethyl]cyclohexan-1-ol
• CAS: 328926-58-5
• 化学式: C₂₅H₅₆O₄Si₃
• 分子量: 504.974
• InChiKey: DKIYOUUGKGIECW-MBDNFAEBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.56
• 重原子数：
  32
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 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-silanyloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-cyclohexanol 在 咪唑 、 碘 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三苯基膦 作用下， 以 甲苯 为溶剂， 生成 (4R,6S)-4,6-Bis-(tert-butyl-dimethyl-silanyloxy)-1-(tert-butyl-dimethyl-silanyloxymethyl)-cyclohexene
  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,3S,5R)-3,5-bis(tert-butyldimethylsilyloxy)-2-methylenecyclohexanol 在 咪唑 、 9-borabicyclo[3.3.1]nonane dimer 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 生成 (1R,2S,3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-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