(4S)-4-[(1R)-1-hydroxy-12-oxooctadecyl]-4-(trityloxymethyl)oxazolidin-2-one | 1421940-47-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: (4S)-4-[(1R)-1-hydroxy-12-oxooctadecyl]-4-(trityloxymethyl)oxazolidin-2-one
• 英文别名: (4S)-4-[(1R)-1-hydroxy-12-oxooctadecyl]-4-(trityloxymethyl)-1,3-oxazolidin-2-one
• CAS: 1421940-47-7
• 化学式: C₄₁H₅₅NO₅
• 分子量: 641.891
• InChiKey: GQHWKZDFCWPRPP-NPTUGSORSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.9
• 重原子数：
  47
• 可旋转键数：
  23
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.51
• 拓扑面积：
  84.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (4S)-4-[(1R)-1-hydroxy-12-oxooctadecyl]-4-(trityloxymethyl)oxazolidin-2-one 在 吡啶 、 4-二甲氨基吡啶 、 对甲苯磺酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 (1R)-1-[(4S)-4-(hydroxymethyl)-2-oxo-1,3-oxazolidin-4-yl]-12-oxooctadecyl benzoate
  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 吡啶 、 4-二甲氨基吡啶 、 20% palladium hydroxide-activated charcoal 、 溶剂黄146 、 lithium hexamethyldisilazane 、 2-碘酰基苯甲酸 作用下， 以 四氢呋喃 、 乙醇 、 水 、 乙腈 为溶剂， 反应 48.0h， 生成 (4S)-4-[(1R)-1-hydroxy-12-oxooctadecyl]-4-(trityloxymethyl)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

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.