(5S,6S)-8,8-dimethyl-2-oxo-3,7,9-trioxa-1-azaspiro[4.5]decane-6-carbaldehyde | 1421940-19-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氮杂螺癸烷衍生物
• 英文名称: (5S,6S)-8,8-dimethyl-2-oxo-3,7,9-trioxa-1-azaspiro[4.5]decane-6-carbaldehyde
• CAS: 1421940-19-3
• 化学式: C₉H₁₃NO₅
• 分子量: 215.206
• InChiKey: CQIISFYAOYMOKO-HZGVNTEJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.78
• 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：

  (5S,6S)-8,8-dimethyl-2-oxo-3,7,9-trioxa-1-azaspiro[4.5]decane-6-carbaldehyde 在 20% palladium hydroxide-activated charcoal 、 溶剂黄146 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 乙醇 、 水 为溶剂， 反应 24.0h， 生成 (4S)-4-[(1R)-1-hydroxy-12-oxooctadecyl]-4-(hydroxymethyl)oxazolidin-2-one
  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：

  (5S,6S)-6-(hydroxymethyl)-8,8-dimethyl-3,7,9-trioxa-1-azaspiro[4.5]decan-2-one 在 2-碘酰基苯甲酸 作用下， 以 乙腈 为溶剂， 以94%的产率得到(5S,6S)-8,8-dimethyl-2-oxo-3,7,9-trioxa-1-azaspiro[4.5]decane-6-carbaldehyde
  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

文献信息

• Stereoselective total synthesis of protected sulfamisterin and its analogues
  作者：Jana Špaková Raschmanová、Miroslava Martinková、Jozef Gonda、Alena Uhríková

  DOI：10.2478/s11696-013-0392-y

  日期：2013.1.1

  The stereoselective synthesis of sulfamisterin I and its unnatural analogues II and V in their protected form was achieved through a common strategy. The Wittig reaction of aldehydes VIII and IX with the C14 hydrophobic side-chain X served as the key C-C connecting transformation. Subsequent functional group inter-conversions in the coupling products XI and XX completed the total synthesis.

  标题：摘要 内容： 通过一种共同的策略，实现了磺胺米斯特林I及其保护形式下的非天然类似物II和V的立体选择性合成。使用韦特反应将醛类化合物VIII和IX与C14疏水侧链X连接，作为关键的C-C连接转化。随后，在偶联产物XI和XX中进行功能团间转化，完成了总合成。
• A stereoselective total synthesis of the HCl salts of mycestericins F, G and ent-F
  作者：Miroslava Martinková、Jozef Gonda、Alena Uhríková、Jana Špaková Raschmanová、Mária Vilková、Beáta Oroszová

  DOI：10.1016/j.tetasy.2012.12.003

  日期：2013.2

  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.