(4S)-4-[(1R)-1-(benzoyloxy)-12-oxooctadecyl]-2-oxo-1,3-oxazolidine-4-carboxylic acid | 1421940-50-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (4S)-4-[(1R)-1-(benzoyloxy)-12-oxooctadecyl]-2-oxo-1,3-oxazolidine-4-carboxylic acid
• 英文别名: (4S)-4-[(1R)-1-benzoyloxy-12-oxooctadecyl]-2-oxo-1,3-oxazolidine-4-carboxylic acid
• CAS: 1421940-50-2
• 化学式: C₂₉H₄₃NO₇
• 分子量: 517.663
• InChiKey: TXEPTKSKVWIEAE-IRPSRAIASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  37
• 可旋转键数：
  21
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.66
• 拓扑面积：
  119
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (4S)-4-[(1R)-1-(benzoyloxy)-12-oxooctadecyl]-2-oxo-1,3-oxazolidine-4-carboxylic acid 在 sodium hydroxide 、 盐酸 作用下， 以 甲醇 、 水 为溶剂， 反应 3.5h， 以62%的产率得到mycestericin G hydrochloride
  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：

  (4S)-4-[(1R)-1-hydroxy-12-oxooctadecyl]-4-(hydroxymethyl)oxazolidin-2-one 在 吡啶 、 4-二甲氨基吡啶 、 sodium dihydrogenphosphate dihydrate 、 sodium chlorite 、 对甲苯磺酸 、 2-碘酰基苯甲酸 作用下， 以 甲醇 、 二氯甲烷 、 水 、 乙腈 、 叔丁醇 为溶剂， 反应 30.5h， 生成 (4S)-4-[(1R)-1-(benzoyloxy)-12-oxooctadecyl]-2-oxo-1,3-oxazolidine-4-carboxylic acid
  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.