(5R,6R)-6-(tert-butyldiphenylsilanyloxymethyl)-5-hydroxymethylcyclohex-2-enone | 1256356-04-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (5R,6R)-6-(tert-butyldiphenylsilanyloxymethyl)-5-hydroxymethylcyclohex-2-enone
• 英文别名: (5R,6R)-6-[[tert-butyl(diphenyl)silyl]oxymethyl]-5-(hydroxymethyl)cyclohex-2-en-1-one
• CAS: 1256356-04-3
• 化学式: C₂₄H₃₀O₃Si
• 分子量: 394.586
• InChiKey: YIZYDLCBMCCWNO-UGKGYDQZSA-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：

  (5R,6R)-6-(tert-butyldiphenylsilanyloxymethyl)-5-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75%的产率得到(2R,3R,5S,6S)-2-(tert-butyldiphenylsilanyloxymethyl)-5,6-dihydroxy-3-(hydroxymethyl)cyclohexanone
  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：

  (5R,6R)-6-(tert-butyldiphenylsilanyloxymethyl)-5-(4-methoxybenzyloxymethyl)cyclohex-2-enone 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 1.0h， 以88%的产率得到(5R,6R)-6-(tert-butyldiphenylsilanyloxymethyl)-5-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.