(1R,3S,5R)-3,5-bis(tert-butyldimethylsilyloxy)-2-methylenecyclohexanol | 121289-21-2

• 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,3S,5R)-3,5-bis(tert-butyldimethylsilyloxy)-2-methylenecyclohexanol
• 英文别名: (1R,3S,5R)-3,5-Bis((tert-butyldimethylsilyl)oxy)-2-methylenecyclohexan-1-ol；(1R,3S,5R)-3,5-bis[[tert-butyl(dimethyl)silyl]oxy]-2-methylidenecyclohexan-1-ol
• CAS: 121289-21-2
• 化学式: C₁₉H₄₀O₃Si₂
• 分子量: 372.696
• InChiKey: OKADFXHGOLLIPI-ZACQAIPSSA-N

物化性质

• 沸点：
  377.8±42.0 °C(Predicted)
• 密度：
  0.92±0.1 g/cm3(Predicted)
• 溶解度：
  溶于丙酮、DCM、DMSO、乙酸乙酯、甲醇

计算性质

• 辛醇/水分配系数(LogP)：
  5.48
• 重原子数：
  24
• 可旋转键数：
  6
• 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,3S,5R)-3,5-bis(tert-butyldimethylsilyloxy)-2-methylenecyclohexanol 在 甲醇 、 4-二甲氨基吡啶 、 chromium chloride 、 sodium periodate 、 lithium aluminium tetrahydride 、 potassium carbonate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 sodium iodide 作用下， 以 四氢呋喃 、 二氯甲烷 、 丙酮 为溶剂， 生成 (3S,5R)-3,5-Bis[(tert-butyldimethylsilyl)oxy]-2-methylcyclohex-1-en-1-carboxaldehyde
  参考文献：
  名称：

  Efficient enantiospecific synthesis of key A-ring synthons for the preparation of 1.alpha.,25-dihydroxyvitamin D3 using a chromium(II)-mediated reaction

  摘要：

  DOI：

  10.1021/jo00276a003
• 作为产物：
  描述：

  (1R,3R,5S,6S)-5-(tert-butyldimethylsilyloxy)-6-methyl-7-oxabicyclo[4.1.0]heptan-3-ol 在 2,2,6,6-四甲基哌啶 、 咪唑 、 正丁基锂 、 氯化二乙基铝 作用下， 以 正己烷 、 N,N-二甲基甲酰胺 、 甲苯 、 苯 为溶剂， 反应 3.0h， 生成 (1R,3S,5R)-3,5-bis(tert-butyldimethylsilyloxy)-2-methylenecyclohexanol
  参考文献：
  名称：

  Enantioselective Approach to the Synthesis of Cyclohexane Carbocyclic Nucleosides

  摘要：

  (R)-(-)-Carvone was used as starting material for the synthesis of a new series of 2-(hydroxymethyl)cyclohexane-1,3-diol nucleosides. The enantioselective precursors of the nucleoside analogues were obtained via a stereo-and regioselective hydroboration reaction. The compounds have equatorial oriented base moieties despite the presence of three other axial substituents.

  DOI：

  10.1021/jo972285c

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
• A Novel and Enantioselective Approach to the Synthesis of Cyclohexane Carbocyclic Nucleosides Starting from (-)-Carvone
  作者：Jing Wang、Piet Herdewijn

  DOI：10.1080/15257779908041504

  日期：1999.4

  3,5-dihydroxy-4-(hydroxymethyl)-1-cyclohexanyl adenine has been synthesized starting from (-)-carvone. The adenine base was introduced via Mitsunobu reaction. Conformational analysis showed that the base still adopts the equatorial position at the expence of three axial substituents.
• 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.
• HATAKEYAMA, SUSUMI;NUMATA, HIROTOSHI;OSANAI, KEN;TAKANO, SEIICHI, J. ORG. CHEM., 54,(1989) N5, C. 3515-3517
  作者：HATAKEYAMA, SUSUMI、NUMATA, HIROTOSHI、OSANAI, KEN、TAKANO, SEIICHI

  DOI：——

  日期：——