(5R,6S)-1-benzyl-6-[(3Z)-1-(2-hexyl-1,3-dioxolan-2-yl)dec-3-en-1-yl]-8,8-dimethyl-3,7,9-trioxa-1-azaspiro[4.5]decan-2-one   | 1421940-34-2

• 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: (5R,6S)-1-benzyl-6-[(3Z)-1-(2-hexyl-1,3-dioxolan-2-yl)dec-3-en-1-yl]-8,8-dimethyl-3,7,9-trioxa-1-azaspiro[4.5]decan-2-one
• 英文别名: (5R,6S)-1-benzyl-6-[(Z)-10-(2-hexyl-1,3-dioxolan-2-yl)dec-3-enyl]-8,8-dimethyl-3,7,9-trioxa-1-azaspiro[4.5]decan-2-one
• CAS: 1421940-34-2
• 化学式: C₃₄H₅₃NO₆
• 分子量: 571.798
• InChiKey: KBZXRBZXDVBALS-AMXPOZSWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.8
• 重原子数：
  41
• 可旋转键数：
  17
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  66.5
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  ethyl (4S)-4-[(4R)-3-benzyl-4-(hydroxymethyl)-2-oxooxazolidin-4-yl]-4-hydroxybutanoate 在 正丁基锂 、 camphor-10-sulfonic acid 、 二异丁基氢化铝 、 lithium hexamethyldisilazane 、 2-碘酰基苯甲酸 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 丙酮 、 乙腈 为溶剂， 反应 7.08h， 生成 (5R,6S)-1-benzyl-6-[(3E)-10-(2-hexyl-1,3-dioxolan-2-yl)dec-3-en-1-yl]-8,8-dimethyl-3,7,9-trioxa-1-azaspiro[4.5]decan-2-one   、 (5R,6S)-1-benzyl-6-[(3Z)-1-(2-hexyl-1,3-dioxolan-2-yl)dec-3-en-1-yl]-8,8-dimethyl-3,7,9-trioxa-1-azaspiro[4.5]decan-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

文献信息

• 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.