(5S,6S)-5-(tert-butyldimethylsilyloxy)-6-[(tert-butyldimethylsilyloxy)methyl]piperidin-2-one | 874483-91-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: (5S,6S)-5-(tert-butyldimethylsilyloxy)-6-[(tert-butyldimethylsilyloxy)methyl]piperidin-2-one
• 英文别名: (5S,6S)-5-[tert-butyl(dimethyl)silyl]oxy-6-[[tert-butyl(dimethyl)silyl]oxymethyl]piperidin-2-one
• CAS: 874483-91-7
• 化学式: C₁₈H₃₉NO₃Si₂
• 分子量: 373.684
• InChiKey: UDMBGENJOZPDHB-GJZGRUSLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.68
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  47.6
• 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-butyldimethylsilyloxy)-6-[(tert-butyldimethylsilyloxy)methyl]piperidin-2-one 在 正丁基锂 、 三氟乙酸 作用下， 以 四氢呋喃 、 吡啶 、 正己烷 为溶剂， -78.0~20.0 ℃ 、101.33 kPa 条件下， 反应 5.67h， 生成 (+)-2-epi-deoxoprosopinine
  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 ammonium cerium(IV) nitrate 作用下， 以 水 、 乙腈 为溶剂， 反应 4.0h， 以64%的产率得到(5S,6S)-5-(tert-butyldimethylsilyloxy)-6-[(tert-butyldimethylsilyloxy)methyl]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