(5S,6S)-5-(tert-butyldimethylsilyloxy)-6-[(tert-butyldimethylsilyloxy)methyl]-1-(4-methoxybenzyl)-5,6-dihydropiperidin-2(1H)-one | 874483-94-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (5S,6S)-5-(tert-butyldimethylsilyloxy)-6-[(tert-butyldimethylsilyloxy)methyl]-1-(4-methoxybenzyl)-5,6-dihydropiperidin-2(1H)-one
• 英文别名: (2S,3S)-3-[tert-butyl(dimethyl)silyl]oxy-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-1-[(4-methoxyphenyl)methyl]-2,3-dihydropyridin-6-one
• CAS: 874483-94-0
• 化学式: C₂₆H₄₅NO₄Si₂
• 分子量: 491.819
• InChiKey: OWMIKJXIDLJGRU-GOTSBHOMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.37
• 重原子数：
  33
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  48
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (5S,6S)-5-(tert-butyldimethylsilyloxy)-6-[(tert-butyldimethylsilyloxy)methyl]-1-(4-methoxybenzyl)-5,6-dihydropiperidin-2(1H)-one 在 四氧化锇 、 N-甲基吗啉氧化物 作用下， 以 叔丁醇 为溶剂， 反应 3.0h， 以75%的产率得到(3S,4R,5R,6S)-5-(tert-butyldimethylsilyloxy)-6-[(tert-butyldimethylsilyloxy)methyl]-3,4-dihydroxy-1-(4-methoxybenzyl)piperidin-2-one
  参考文献：
  名称：

  A new approach for the asymmetric syntheses of 2-epi-deoxoprosopinine and azasugar derivatives

  摘要：

  A new approach to 2-epi-deoxoprosopinine 11, 1-deoxygulonojirimycin 7, and L-gulono-1,5-lactam 9 was described. The C-2 hydroxymethyl group was introduced regioselectively using SMI2 mediated coupling of (S)-3-silyloxyglutarimide 13b with either chloromethyl benzyl ether 16a or the Beau-Skrydstrup reagent 16b, followed by debenzylation and highly cis-diastereoselective reductive deoxygenation. Adoption of the Savoi's chemoselective ring-opening alkylation method allowed a highly diastereoselective introduction of the lipid side chain of 2-epi-deoxoprosopinine 11 in a straightforward manner. Dehydration followed by highly trans-diastereoselective dihydroxylation led to polyoxygenated lactam derivative 27 as a key intermediate for the syntheses of 7 and 9. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.09.112
• 作为产物：
  描述：

  (5S,6S)-5-(tert-butyldimethylsilyloxy)-6-[(tert-butyldimethylsilyloxy)methyl]-1-(4-methoxybenzyl)piperidin-2-one 在 双氧水 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 8.5h， 生成 (5S,6S)-5-(tert-butyldimethylsilyloxy)-6-[(tert-butyldimethylsilyloxy)methyl]-1-(4-methoxybenzyl)-5,6-dihydropiperidin-2(1H)-one
  参考文献：
  名称：

  A new approach for the asymmetric syntheses of 2-epi-deoxoprosopinine and azasugar derivatives

  摘要：

  A new approach to 2-epi-deoxoprosopinine 11, 1-deoxygulonojirimycin 7, and L-gulono-1,5-lactam 9 was described. The C-2 hydroxymethyl group was introduced regioselectively using SMI2 mediated coupling of (S)-3-silyloxyglutarimide 13b with either chloromethyl benzyl ether 16a or the Beau-Skrydstrup reagent 16b, followed by debenzylation and highly cis-diastereoselective reductive deoxygenation. Adoption of the Savoi's chemoselective ring-opening alkylation method allowed a highly diastereoselective introduction of the lipid side chain of 2-epi-deoxoprosopinine 11 in a straightforward manner. Dehydration followed by highly trans-diastereoselective dihydroxylation led to polyoxygenated lactam derivative 27 as a key intermediate for the syntheses of 7 and 9. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.09.112