(S)-5-(tert-butyldimethylsilyloxy)pentane-1,4-diol | 1187785-03-0

• 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: (S)-5-(tert-butyldimethylsilyloxy)pentane-1,4-diol
• 英文别名: (4S)-5-[tert-butyl(dimethyl)silyl]oxypentane-1,4-diol
• CAS: 1187785-03-0
• 化学式: C₁₁H₂₆O₃Si
• 分子量: 234.411
• InChiKey: RBGRDXKJTVXCPM-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.14
• 重原子数：
  15
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-5-(tert-butyldimethylsilyloxy)pentane-1,4-diol 、 乙酰氯 在 2,4,6-三甲基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 7.0h， 以88%的产率得到(S)-5-[(tert-butyldimethylsilyl)oxy]-4-hydroxypent-1-yl acetate
  参考文献：
  名称：

  A radical mediated approach to the stereoselective formal total synthesis of (+)-Sch 642305

  摘要：

  A formal total synthesis of (+)-Sch-642305 is described. The synthesis, which commenced from a simple chiral synthon (5S)-5-(hydroxymethyl)dihydrofuran-2(3H)-one, employed, as a key step, a radical mediated opening of a chiral epoxy alcohol intermediate with Cp(2)Ti(III)Cl following an efficient method developed by us earlier. The resultant intermediate radical was intramolecularly trapped by the electron deficient double bond present in the molecule to give rise to its highly functionalized six-membered carbocyclic ring in stereoselective manner. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.06.059
• 作为产物：
  描述：

  (5S)-(5-tert-butyldimethylsilyloxymethyl)furan-2(5H)-one 在 锂硼氢 、 氯化铵 作用下， 以 四氢呋喃 、 水 为溶剂， 以95%的产率得到(S)-5-(tert-butyldimethylsilyloxy)pentane-1,4-diol
  参考文献：
  名称：

  A radical mediated approach to the stereoselective formal total synthesis of (+)-Sch 642305

  摘要：

  A formal total synthesis of (+)-Sch-642305 is described. The synthesis, which commenced from a simple chiral synthon (5S)-5-(hydroxymethyl)dihydrofuran-2(3H)-one, employed, as a key step, a radical mediated opening of a chiral epoxy alcohol intermediate with Cp(2)Ti(III)Cl following an efficient method developed by us earlier. The resultant intermediate radical was intramolecularly trapped by the electron deficient double bond present in the molecule to give rise to its highly functionalized six-membered carbocyclic ring in stereoselective manner. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.06.059

文献信息

• A radical mediated approach to the stereoselective formal total synthesis of (+)-Sch 642305
  作者：Tushar Kanti Chakraborty、Rajarshi Samanta、Pulukuri Kiran Kumar

  DOI：10.1016/j.tet.2009.06.059

  日期：2009.8

  A formal total synthesis of (+)-Sch-642305 is described. The synthesis, which commenced from a simple chiral synthon (5S)-5-(hydroxymethyl)dihydrofuran-2(3H)-one, employed, as a key step, a radical mediated opening of a chiral epoxy alcohol intermediate with Cp(2)Ti(III)Cl following an efficient method developed by us earlier. The resultant intermediate radical was intramolecularly trapped by the electron deficient double bond present in the molecule to give rise to its highly functionalized six-membered carbocyclic ring in stereoselective manner. (C) 2009 Elsevier Ltd. All rights reserved.