(R)-1-(benzyloxy)-1-((4R,5R)-5-(5-(benzyloxy)pentyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-19-hydroxynonadecan-4-one | 1269799-12-3

• 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: (R)-1-(benzyloxy)-1-((4R,5R)-5-(5-(benzyloxy)pentyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-19-hydroxynonadecan-4-one
• 英文别名: (1R)-1-[(4R,5R)-2,2-dimethyl-5-(5-phenylmethoxypentyl)-1,3-dioxolan-4-yl]-19-hydroxy-1-phenylmethoxynonadecan-4-one
• CAS: 1269799-12-3
• 化学式: C₄₃H₆₈O₆
• 分子量: 681.009
• InChiKey: OWRAGGSWBKDZOS-ILGLXFKISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.5
• 重原子数：
  49
• 可旋转键数：
  30
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  74.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (R)-1-(benzyloxy)-1-((4R,5R)-5-(5-(benzyloxy)pentyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-19-hydroxynonadecan-4-one 在 iron(III) chloride hexahydrate 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以94%的产率得到15-((1R,2R,5S,7R)-2-(benzyloxy)-7-(5-(benzyloxy)pentyl)-6,8-dioxabicyclo[3.2.1]octan-5-yl)pentadecan-1-ol
  参考文献：
  名称：

  Formal total synthesis of (+)-didemniserinolipid B

  摘要：

  The formal total synthesis of (+)-didemniserinolipid B, a marine tunicate possessing a 6,8-dioxabicyclo[3.2.1]octane framework, was accomplished starting from L-(+)-tartaric acid. The key transformations in the synthesis include the elaboration of a gamma-hydroxy-amide readily obtained by desymmetrization of tartaric acid bis-amide via the controlled addition of a Grignard reagent followed by stereoselective reduction of the resulting ketone. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.11.006
• 作为产物：
  描述：

  (R)-1-(benzyloxy)-1-((4S,5R)-5-(5-(benzyloxy)pentyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-19-hydroxynonadec-2-en-4-one 在 10% palladium on activated charcoal 、 氢气 、 碳酸氢钠 作用下， 以 正己烷 为溶剂， 以87%的产率得到(R)-1-(benzyloxy)-1-((4R,5R)-5-(5-(benzyloxy)pentyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-19-hydroxynonadecan-4-one
  参考文献：
  名称：

  Formal total synthesis of (+)-didemniserinolipid B

  摘要：

  The formal total synthesis of (+)-didemniserinolipid B, a marine tunicate possessing a 6,8-dioxabicyclo[3.2.1]octane framework, was accomplished starting from L-(+)-tartaric acid. The key transformations in the synthesis include the elaboration of a gamma-hydroxy-amide readily obtained by desymmetrization of tartaric acid bis-amide via the controlled addition of a Grignard reagent followed by stereoselective reduction of the resulting ketone. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.11.006

文献信息

• Formal total synthesis of (+)-didemniserinolipid B
  作者：Kavirayani R. Prasad、Vasudeva Rao Gandi

  DOI：10.1016/j.tetasy.2010.11.006

  日期：2010.12

  The formal total synthesis of (+)-didemniserinolipid B, a marine tunicate possessing a 6,8-dioxabicyclo[3.2.1]octane framework, was accomplished starting from L-(+)-tartaric acid. The key transformations in the synthesis include the elaboration of a gamma-hydroxy-amide readily obtained by desymmetrization of tartaric acid bis-amide via the controlled addition of a Grignard reagent followed by stereoselective reduction of the resulting ketone. (C) 2010 Elsevier Ltd. All rights reserved.