(1S,2S,4S,5S)-4,5-bis(tert-butyldimethylsilyloxy)cyclohexane-1,2-diol | 167611-57-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S,2S,4S,5S)-4,5-bis(tert-butyldimethylsilyloxy)cyclohexane-1,2-diol
• 英文别名: (1S,2S,4S,5S)-4,5-bis[[tert-butyl(dimethyl)silyl]oxy]cyclohexane-1,2-diol
• CAS: 167611-57-6
• 化学式: C₁₈H₄₀O₄Si₂
• 分子量: 376.684
• InChiKey: XNZYUZZBJHEYPA-VGWMRTNUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.28
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 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：

  丙酮 、 (1S,2S,4S,5S)-4,5-bis(tert-butyldimethylsilyloxy)cyclohexane-1,2-diol 在 对甲苯磺酸 作用下， 以68%的产率得到(3aS,5S,6S,7aS)-5,6-Bis-(tert-butyl-dimethyl-silanyloxy)-2,2-dimethyl-hexahydro-benzo[1,3]dioxole
  参考文献：
  名称：

  Highly enantio- and diastereo-selective synthesis of C2-symmetric 3,5-cyclohexadiene-1,2-diol and D2-symmetric cyclohexane-1,2,4,5-tetrol

  摘要：

  Highly enantio- and diastereo-selective synthesis of C-2-symmetric 3,5-cyclohexadiene-1,2-diol 5 and D-2-symmetric cyclohexane-1,2,4,5-tetrol related compounds 7a,b, 10, 11 has been achieved using optically active 4-cyclohexene-1,2-diol (S,S)-1c prepared by an enzymatic procedure.

  DOI：

  10.1016/0957-4166(94)00350-k
• 作为产物：
  描述：

  (4S,5S)-4,5-dihydroxyocta-1,7-diene 在 Cp2Ti(Ph)Cl 4-二甲氨基吡啶 、 三甲基氯硅烷 、 氧气 、 臭氧 、 三乙胺 、 锌 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 33.67h， 生成 (1S,2S,4S,5S)-4,5-bis(tert-butyldimethylsilyloxy)cyclohexane-1,2-diol
  参考文献：
  名称：

  Diastereoselective Inter- and Intramolecular Pinacol Coupling of Aldehydes Promoted by Monomeric Titanocene(III) Complex Cp₂TiPh

  摘要：

  A monomeric titanocene(III) derivative, Cp2TiPh, effectively promoted the pinacol coupling of both an aromatic aldehyde, benzaldehyde, and an aliphatic aldehyde, 3-phenylpropionaldehyde. The same reactive complex was successfully generated by a catalytic amount of a precursor, Cp2Ti-(PH)Cl and its stoichiometric amount of Zn. The Cp2TiPh-catalyzed pinacol coupling of benzaldehyde derivatives and aliphatic aldehydes afforded the corresponding 1,2-diols in high yields with moderate to good three-selectivity. On the other hand, Cp2TiPh-catalyzed pinacol cyclization of dials gave cyclic 1,2-diols with excellent diastereoselectivity. The extension of this protocol to chiral dials demonstrated that the phenyltitanium complex catalytically transmitted an axial chirality or a central chirality of the starting dials to the central chirality of the resultant l,a-diols.

  DOI：

  10.1021/jo001781p