tert-butyl (5S,6R)-6-[10-(2-hexyl-1,3-dioxolan-2-yl)decyl]-8,8-dimethyl-2-oxo-3,7,9-trioxa-1-azaspiro[4.5]decane-1-carboxylate | 1421940-55-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: tert-butyl (5S,6R)-6-[10-(2-hexyl-1,3-dioxolan-2-yl)decyl]-8,8-dimethyl-2-oxo-3,7,9-trioxa-1-azaspiro[4.5]decane-1-carboxylate
• CAS: 1421940-55-7
• 化学式: C₃₂H₅₇NO₈
• 分子量: 583.806
• InChiKey: QUURKKSGYSLKNK-MXBOTTGLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.88
• 重原子数：
  41.0
• 可旋转键数：
  16.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  92.76
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  tert-butyl (5S,6R)-6-[10-(2-hexyl-1,3-dioxolan-2-yl)decyl]-8,8-dimethyl-2-oxo-3,7,9-trioxa-1-azaspiro[4.5]decane-1-carboxylate 在 caesium carbonate 作用下， 以 甲醇 为溶剂， 反应 1.5h， 以92%的产率得到tert-butyl (5S,6R)-6-[10-(2-hexyl-1,3-dioxolan-2-yl)decyl]-8,8-dimethyl-2-oxo-3,7,9-trioxa-1-azaspiro[4.5]decane-1-carboxylate
  参考文献：
  名称：

  A stereoselective total synthesis of the HCl salts of mycestericins F, G and ent-F

  摘要：

  The total synthesis of the HCl salts of two natural sphingolipid-related amino acid derivatives, mycestericins F 4 and G 5 together with unnatural ent-4 center dot HCl, starting from the four crucial scaffolds 6, 8, 9, 11 and utilizing the Wittig reaction to build the C-20 backbone, has been achieved. The selection of selective functional group interconversions accompanied with suitable protection-deprotection protocols in the coupling products 20 and 34 gave the desired structures. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.12.003
• 作为产物：
  描述：

  [9-(2-hexyl-1,3-dioxolan-2-yl)nonyl]triphenylphosphonium bromide 在 4-二甲氨基吡啶 、 20% palladium hydroxide-activated charcoal 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 乙醇 、 乙腈 为溶剂， 反应 2.5h， 生成 tert-butyl (5S,6R)-6-[10-(2-hexyl-1,3-dioxolan-2-yl)decyl]-8,8-dimethyl-2-oxo-3,7,9-trioxa-1-azaspiro[4.5]decane-1-carboxylate
  参考文献：
  名称：

  A stereoselective total synthesis of the HCl salts of mycestericins F, G and ent-F

  摘要：

  The total synthesis of the HCl salts of two natural sphingolipid-related amino acid derivatives, mycestericins F 4 and G 5 together with unnatural ent-4 center dot HCl, starting from the four crucial scaffolds 6, 8, 9, 11 and utilizing the Wittig reaction to build the C-20 backbone, has been achieved. The selection of selective functional group interconversions accompanied with suitable protection-deprotection protocols in the coupling products 20 and 34 gave the desired structures. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.12.003