(5S)-5-[tert-butyl(dimethyl)silyl]oxy-6-hydroxy-1-[(4-methoxyphenyl)methyl]-6-(phenylmethoxymethyl)piperidin-2-one | 874483-86-0

• 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)-5-[tert-butyl(dimethyl)silyl]oxy-6-hydroxy-1-[(4-methoxyphenyl)methyl]-6-(phenylmethoxymethyl)piperidin-2-one
• CAS: 874483-86-0
• 化学式: C₂₇H₃₉NO₅Si
• 分子量: 485.696
• InChiKey: QMSRWTQSUADKRP-BXXZMZEQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.11
• 重原子数：
  34
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  68.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (5S)-5-[tert-butyl(dimethyl)silyl]oxy-6-hydroxy-1-[(4-methoxyphenyl)methyl]-6-(phenylmethoxymethyl)piperidin-2-one 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 20.0 ℃ 、101.32 kPa 条件下， 反应 8.0h， 以90%的产率得到2-Piperidinone,5-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-6-hydroxy-6-(hydroxymethyl)-1-[(4-methoxyphenyl)methyl]-, (5S)-
  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：

  苄基氯甲基醚 、 (3S)-3-[tert-butyl(dimethyl)silyl]oxy-1-[(4-methoxyphenyl)methyl]piperidine-2,6-dione 在 samarium diiodide 作用下， 以 四氢呋喃 为溶剂， 反应 0.75h， 以67%的产率得到(5S)-5-[tert-butyl(dimethyl)silyl]oxy-6-hydroxy-1-[(4-methoxyphenyl)methyl]-6-(phenylmethoxymethyl)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.