ethyl 2-[(1R,2R,6S)-6-(tert-butyldimethylsilyloxy)-2-{(R)-5-hydroxyhexyl}-3-oxocyclohexyl]acetate | 960492-29-9

• 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: ethyl 2-[(1R,2R,6S)-6-(tert-butyldimethylsilyloxy)-2-{(R)-5-hydroxyhexyl}-3-oxocyclohexyl]acetate
• 英文别名: ethyl 2-[(1R,2R,6S)-6-[tert-butyl(dimethyl)silyl]oxy-2-[(5R)-5-hydroxyhexyl]-3-oxocyclohexyl]acetate
• CAS: 960492-29-9
• 化学式: C₂₂H₄₂O₅Si
• 分子量: 414.658
• InChiKey: UDUBHZUGEICNSX-MLYOOKFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.87
• 重原子数：
  28
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 2-[(1R,2R,6S)-6-(tert-butyldimethylsilyloxy)-2-{(R)-5-hydroxyhexyl}-3-oxocyclohexyl]acetate 在 4-二甲氨基吡啶 、 2,4,6-三氯苯甲酰氯 、 potassium trimethylsilonate 、 四丁基氟化铵 、 sodium hexamethyldisilazane 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 91.75h， 生成 (+)-11-epi-Sch 642305
  参考文献：
  名称：

  Stereoselective synthesis of the bacterial DNA primase inhibitor Sch 642305 and its C-4 epimer

  摘要：

  A convergent stereoselective synthesis of the bacterial DNA primase inhibitor Sch 642305 and its non-natural epimer at C-4 is described. A key aspect was the construction of a trans-2,3-disubstituted cyclohexanone system by means of a stereoselective Michael addition/alpha-alkylation sequence. The macrolactone ring of either stereoisorner was created using the Mitsunobu and Yamaguchi procedures, respectively. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.09.080
• 作为产物：
  描述：

  在 10% palladium on activated carbon 、 氢气 作用下， 以 乙醇 为溶剂， 反应 12.0h， 以75%的产率得到ethyl 2-[(1R,2R,6S)-6-(tert-butyldimethylsilyloxy)-2-{(R)-5-hydroxyhexyl}-3-oxocyclohexyl]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

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.
• Stereoselective synthesis of the bacterial DNA primase inhibitor Sch 642305 and its C-4 epimer
  作者：Jorge García-Fortanet、Miguel Carda、J. Alberto Marco

  DOI：10.1016/j.tet.2007.09.080

  日期：2007.12

  A convergent stereoselective synthesis of the bacterial DNA primase inhibitor Sch 642305 and its non-natural epimer at C-4 is described. A key aspect was the construction of a trans-2,3-disubstituted cyclohexanone system by means of a stereoselective Michael addition/alpha-alkylation sequence. The macrolactone ring of either stereoisorner was created using the Mitsunobu and Yamaguchi procedures, respectively. (c) 2007 Elsevier Ltd. All rights reserved.