(+/-)-cis/trans-2-{[(tert-butyl)(dimethyl)silyloxy]methyl}cyclohexanol | 832131-69-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (+/-)-cis/trans-2-{[(tert-butyl)(dimethyl)silyloxy]methyl}cyclohexanol
• 英文别名: (+/-)-cis/trans-2-(tert-butyldimethylsilyloxymethyl)cyclohexanol；2-({[tert-Butyl(dimethyl)silyl]oxy}methyl)cyclohexan-1-ol；2-[[tert-butyl(dimethyl)silyl]oxymethyl]cyclohexan-1-ol
• CAS: 832131-69-8
• 化学式: C₁₃H₂₈O₂Si
• 分子量: 244.45
• InChiKey: XAXDWAKVUCNTJV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.56
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (+/-)-cis/trans-2-{[(tert-butyl)(dimethyl)silyloxy]methyl}cyclohexanol 在 silica gel 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 14.0h， 生成 C₁₃H₂₆O₂Si
  参考文献：
  名称：

  A Boron-Based Synthesis of the Natural Product (+)-trans-Dihydrolycoricidine

  摘要：

  DOI：

  10.1002/anie.201007135
• 作为产物：
  描述：

  2-环己酮甲酸乙酯 在 咪唑 、 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 7.5h， 生成 (+/-)-cis/trans-2-{[(tert-butyl)(dimethyl)silyloxy]methyl}cyclohexanol
  参考文献：
  名称：

  1,2-Disubstituted cyclohexane nucleosides: comparative study for the synthesis of cis and trans adenosine analogues

  摘要：

  A new class of adenosine analogues with 1,2-disubstituted carbocycles (with cis and trans stereochemistry) have been synthesized. Construction of the base on the amino group of (+/-)-cis-(2-aminocyclohexyl)methanol was more efficient than the Mitsunobu condensation between the purine base and protected (+/-)-trans-(2-hydroxymethyl)cyclohexanol. The latter strategy gave the final compound with cis stereochemistry in a short number of steps with the overall yield depending on the nature of the protecting group on the hydroxymethyl group of the diol. However, Mitsunobu condensation between a purine base and the protected (+/-)-cis-(2-hydroxymethyl)cyclohexanol is not an ideal method to obtain trans purine derivatives because the elimination reaction is faster than the substitution reaction. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.10.076

文献信息

• Synthesis of Carbocyclic Pyrimidine Nucleosides Using the<i>Mitsunobu</i>Reaction:<i>O</i>²-<i>vs. N</i>¹-Alkylation
  作者：Elías Quezada、Dolores Viña、Giovanna Delogu、Fernanda Borges、Lourdes Santana、Eugenio Uriarte

  DOI：10.1002/hlca.200900242

  日期：2010.2

  The Mitsunobu reaction is an important tool in carbocyclic nucleoside chemistry for the direct coupling of alcohols with heterocyclic bases under mild conditions. Chemical evidences for an unusual competitive O2‐ vs. N1‐alkylation of 3‐substituted pyrimidines is presented.

  该光延反应是在碳环核苷化学与温和的条件下杂环碱醇的直接耦合的重要工具。对于一个不寻常的竞争性化学证据ö 2 -与Ñ 1的3-取代的嘧啶烷基化呈现。
• Therapeutic compounds for treating dyslipidemic conditions
  申请人：Jones Brian A.

  公开号：US20050239769A1

  公开（公告）日：2005-10-27

  The present invention relates to novel LXR ligands of Formula I and the pharmaceutically acceptable salts, esters and tautomers thereof, which are useful in the treatment of dyslipidemic conditions, particularly depressed levels of HDL cholesterol.

  本发明涉及公式I的新型LXR配体及其药学上可接受的盐、酯和互变异构体，其在治疗脂质代谢异常症状，特别是低下的高密度脂蛋白胆固醇水平中有用。
• A Boron-Based Synthesis of the Natural Product (+)-trans-Dihydrolycoricidine
  作者：Sarah L. Poe、James P. Morken

  DOI：10.1002/anie.201007135

  日期：2011.4.26
• 1,2-Disubstituted cyclohexane nucleosides: comparative study for the synthesis of cis and trans adenosine analogues
  作者：Dolores Viña、Lourdes Santana、Eugenio Uriarte、Carmen Terán

  DOI：10.1016/j.tet.2004.10.076

  日期：2005.1

  A new class of adenosine analogues with 1,2-disubstituted carbocycles (with cis and trans stereochemistry) have been synthesized. Construction of the base on the amino group of (+/-)-cis-(2-aminocyclohexyl)methanol was more efficient than the Mitsunobu condensation between the purine base and protected (+/-)-trans-(2-hydroxymethyl)cyclohexanol. The latter strategy gave the final compound with cis stereochemistry in a short number of steps with the overall yield depending on the nature of the protecting group on the hydroxymethyl group of the diol. However, Mitsunobu condensation between a purine base and the protected (+/-)-cis-(2-hydroxymethyl)cyclohexanol is not an ideal method to obtain trans purine derivatives because the elimination reaction is faster than the substitution reaction. (C) 2004 Elsevier Ltd. All rights reserved.