tert-butyl [(2S,3S)-1,3-bis(tert-butyldimethylsilyloxy)-6-oxooctadecan]-2-yl-carbamate | 1055032-95-5

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: tert-butyl [(2S,3S)-1,3-bis(tert-butyldimethylsilyloxy)-6-oxooctadecan]-2-yl-carbamate
• 英文别名: tert-butyl N-[(2S,3S)-1,3-bis[[tert-butyl(dimethyl)silyl]oxy]-6-oxooctadecan-2-yl]carbamate
• CAS: 1055032-95-5
• 化学式: C₃₅H₇₃NO₅Si₂
• 分子量: 644.139
• InChiKey: JRDHEULVYNMYBQ-CONSDPRKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.95
• 重原子数：
  43
• 可旋转键数：
  25
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  73.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  tert-butyl [(2S,3S)-1,3-bis(tert-butyldimethylsilyloxy)-6-oxooctadecan]-2-yl-carbamate 在 palladium dihydroxide 三氟乙酸 、 氢气 作用下， 以 乙醇 为溶剂， 20.0 ℃ 、101.32 kPa 条件下， 反应 5.0h， 以51%的产率得到(+)-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]piperidin-2-one 在 正丁基锂 作用下， 以 四氢呋喃 、 吡啶 、 正己烷 为溶剂， 反应 0.67h， 生成 tert-butyl [(2S,3S)-1,3-bis(tert-butyldimethylsilyloxy)-6-oxooctadecan]-2-yl-carbamate
  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