(5S,6S)-5-(tert-butyldiphenylsilanyloxymethyl)-6-hydroxymethylcyclohex-2-enone | 1256355-92-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (5S,6S)-5-(tert-butyldiphenylsilanyloxymethyl)-6-hydroxymethylcyclohex-2-enone
• 英文别名: (5S,6S)-5-[[tert-butyl(diphenyl)silyl]oxymethyl]-6-(hydroxymethyl)cyclohex-2-en-1-one
• CAS: 1256355-92-6
• 化学式: C₂₄H₃₀O₃Si
• 分子量: 394.586
• InChiKey: QQKNCMBULVVQLO-DENIHFKCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.32
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (5S,6S)-5-(tert-butyldiphenylsilanyloxymethyl)-6-hydroxymethylcyclohex-2-enone 在 甲基磺酰胺 、 AD-mix-α 、 水 作用下， 以 叔丁醇 为溶剂， 反应 24.0h， 以76%的产率得到(2S,3S,5S,6S)-3-(tert-butyldiphenylsilanyloxymethyl)-5,6-dihydroxy-2-hydroxymethylcyclohexanone
  参考文献：
  名称：

  Asymmetric synthesis of hydroxy-skipped bishomo-inositols as potential glycosidase inhibitors

  摘要：

  Four isomeric hydroxy-skipped bishomo-inositol analogs have been synthesized from both enantiomers of 5-hydroxymethyl-2-cyclohexenone. Sharpless asymmetric dihydroxylation and substrate-directed anionic hydroxymethylation are the key reactions which have been employed successfully for the synthesis of new cyclitols. The synthesized cyclitols have been screened for their inhibitory effect on alpha- and beta-glycosidases. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.07.033
• 作为产物：
  描述：

  1H-苯并三唑-1-甲醇 、 (S)-5-(tert-butyldiphenylsilanyloxymethyl)cyclohex-2-enone 在 2,2,6,6-tetramethylpiperidinyl-lithium 、 水 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以80%的产率得到(5S,6S)-5-(tert-butyldiphenylsilanyloxymethyl)-6-hydroxymethylcyclohex-2-enone
  参考文献：
  名称：

  Asymmetric synthesis of hydroxy-skipped bishomo-inositols as potential glycosidase inhibitors

  摘要：

  Four isomeric hydroxy-skipped bishomo-inositol analogs have been synthesized from both enantiomers of 5-hydroxymethyl-2-cyclohexenone. Sharpless asymmetric dihydroxylation and substrate-directed anionic hydroxymethylation are the key reactions which have been employed successfully for the synthesis of new cyclitols. The synthesized cyclitols have been screened for their inhibitory effect on alpha- and beta-glycosidases. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.07.033

文献信息

• Asymmetric synthesis of hydroxy-skipped bishomo-inositols as potential glycosidase inhibitors
  作者：Tridib Mahapatra、Samik Nanda

  DOI：10.1016/j.tetasy.2010.07.033

  日期：2010.9

  Four isomeric hydroxy-skipped bishomo-inositol analogs have been synthesized from both enantiomers of 5-hydroxymethyl-2-cyclohexenone. Sharpless asymmetric dihydroxylation and substrate-directed anionic hydroxymethylation are the key reactions which have been employed successfully for the synthesis of new cyclitols. The synthesized cyclitols have been screened for their inhibitory effect on alpha- and beta-glycosidases. (C) 2010 Elsevier Ltd. All rights reserved.