(R,E)-1-(benzyloxy)-1-((4S,5R)-5-(5-(benzyloxy)pentyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-19-hydroxynonadec-2-en-4-one | 1269799-10-1

• 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,E)-1-(benzyloxy)-1-((4S,5R)-5-(5-(benzyloxy)pentyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-19-hydroxynonadec-2-en-4-one
• 英文别名: (E,1R)-1-[(4S,5R)-2,2-dimethyl-5-(5-phenylmethoxypentyl)-1,3-dioxolan-4-yl]-19-hydroxy-1-phenylmethoxynonadec-2-en-4-one
• CAS: 1269799-10-1
• 化学式: C₄₃H₆₆O₆
• 分子量: 678.993
• InChiKey: HEQZCEMVLVTKPV-PHDMVIOTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.4
• 重原子数：
  49
• 可旋转键数：
  29
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  74.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  (4R,5R)-5-(6-(benzyloxy)hexanoyl)-N,N,2,2-tetramethyl-1,3-dioxolane-4-carboxamide 在 甲醇 、 sodium tetrahydroborate 、 cerium(III) chloride heptahydrate 、 偶氮二甲酸二异丙酯 、 potassium carbonate 、 caesium carbonate 、 对甲苯磺酸 、 三苯基膦 、 silver(l) oxide 、 2-碘酰基苯甲酸 作用下， 以 四氢呋喃 、 甲醇 、 乙酸乙酯 、 异丙醇 、 甲苯 、 苯 为溶剂， 反应 26.75h， 生成 (R,Z)-1-(benzyloxy)-1-((4S,5R)-5-(5-(benzyloxy)pentyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-19-hydroxynonadec-2-en-4-one 、 (R,E)-1-(benzyloxy)-1-((4S,5R)-5-(5-(benzyloxy)pentyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-19-hydroxynonadec-2-en-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.