(5S,6S)-5-(tert-butyldimethylsilyloxy)-6-(hydroxymethyl)-1-(4-methoxybenzyl)piperidin-2-one | 874483-89-3

• 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-(hydroxymethyl)-1-(4-methoxybenzyl)piperidin-2-one
• 英文别名: (5S,6S)-5-[tert-butyl(dimethyl)silyl]oxy-6-(hydroxymethyl)-1-[(4-methoxyphenyl)methyl]piperidin-2-one
• CAS: 874483-89-3
• 化学式: C₂₀H₃₃NO₄Si
• 分子量: 379.572
• InChiKey: XIAVRWMXAHLMQJ-ROUUACIJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.57
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  59
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (5S,6S)-5-(tert-butyldimethylsilyloxy)-6-(hydroxymethyl)-1-(4-methoxybenzyl)piperidin-2-one 在 咪唑 、 4-二甲氨基吡啶 、 正丁基锂 、 ammonium cerium(IV) nitrate 、 三氟乙酸 作用下， 以 四氢呋喃 、 吡啶 、 正己烷 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， -78.0~20.0 ℃ 、101.33 kPa 条件下， 反应 21.67h， 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：

  (3S)-3-[tert-butyl(dimethyl)silyl]oxy-1-[(4-methoxyphenyl)methyl]piperidine-2,6-dione 在 palladium on activated charcoal 三乙基硅烷 、 samarium diiodide 、 三氟化硼乙醚 、 氢气 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， -78.0~20.0 ℃ 、101.33 kPa 条件下， 反应 8.17h， 生成 (5S,6S)-5-(tert-butyldimethylsilyloxy)-6-(hydroxymethyl)-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

文献信息

• A new approach for the asymmetric syntheses of 2-epi-deoxoprosopinine and azasugar derivatives
  作者：Bang-Guo Wei、Jie Chen、Pei-Qiang Huang

  DOI：10.1016/j.tet.2005.09.112

  日期：2006.1

  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.