(R)-1,2-O-Diacetylglycerol | 133398-61-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 甘油脂
• 英文名称: (R)-1,2-O-Diacetylglycerol
• 英文别名: R-2,3-Diacetoxypropan-1-ol；[(2R)-2-acetyloxy-3-hydroxypropyl] acetate
• CAS: 133398-61-5
• 化学式: C₇H₁₂O₅
• 分子量: 176.169
• InChiKey: UXDDRFCJKNROTO-SSDOTTSWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  12
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (R)-1,2-O-Diacetylglycerol 在 四(三苯基膦)钯 copper(l) iodide 、 三正丁胺 、 mercury(II) diacetate 、 溴 、 正丁胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 27.0h， 生成 Petrosyne Ia triacetate
  参考文献：
  名称：

  Structure and synthesis of petrosynes, new acetylenic enol ether glycerides from the Okinawan marine sponge of the genus Petrosia

  摘要：

  Acetylenic enol ether glycerides, 1 and 3, were found in the Okinawan marine sponge of the genus Petrosia. The plane structures of these glycerides were deduced from spectroscopic analysis. Their complete structures were established by enantioselective total synthesis of all possible stereoisomers using (R)-1-O-benzylglycerol and its (S)-enantiomer, prepared from D-mannitol and L-ascorbic acid, respectively, as chiral building blocks. The synthesis involves the palladium(O)-catalyzed coupling reaction of bromo enol ether 9 with enediyne 21 as a key step. It became evident from the synthesis that the natural product 1 consisted of a mixture of (7R,2'S)-24 (petrosyne Ia) and (7S,2S)-24 (petrosyne Ib), and the natural product 3 consisted of a mixture of (7R,2'S)-28 (petrosyne IIa) and (7S,2'S)-28 (petrosyne IIb).

  DOI：

  10.1021/jo00073a030
• 作为产物：
  描述：

  (2R)-1,2-diacetoxy-3-(benzyloxy)propane 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 10.0h， 以99%的产率得到(R)-1,2-O-Diacetylglycerol
  参考文献：
  名称：

  Structure and synthesis of petrosynes, new acetylenic enol ether glycerides from the Okinawan marine sponge of the genus Petrosia

  摘要：

  Acetylenic enol ether glycerides, 1 and 3, were found in the Okinawan marine sponge of the genus Petrosia. The plane structures of these glycerides were deduced from spectroscopic analysis. Their complete structures were established by enantioselective total synthesis of all possible stereoisomers using (R)-1-O-benzylglycerol and its (S)-enantiomer, prepared from D-mannitol and L-ascorbic acid, respectively, as chiral building blocks. The synthesis involves the palladium(O)-catalyzed coupling reaction of bromo enol ether 9 with enediyne 21 as a key step. It became evident from the synthesis that the natural product 1 consisted of a mixture of (7R,2'S)-24 (petrosyne Ia) and (7S,2S)-24 (petrosyne Ib), and the natural product 3 consisted of a mixture of (7R,2'S)-28 (petrosyne IIa) and (7S,2'S)-28 (petrosyne IIb).

  DOI：

  10.1021/jo00073a030

文献信息

• Dérivés d'acide phosphonique, leur procédé de préparation et les compositions pharmaceutiques qui les contiennent
  申请人：ADIR ET COMPAGNIE

  公开号：EP0639586B1

  公开（公告）日：2001-03-21
• US5481030A
  申请人：——

  公开号：US5481030A

  公开（公告）日：1996-01-02
• US5608045A
  申请人：——

  公开号：US5608045A

  公开（公告）日：1997-03-04
• US5591728A
  申请人：——

  公开号：US5591728A

  公开（公告）日：1997-01-07
• Structure and synthesis of petrosynes, new acetylenic enol ether glycerides from the Okinawan marine sponge of the genus Petrosia
  作者：Kazuo Iguchi、Makoto Kitade、Toshihiko Kashiwagi、Yasuji Yamada

  DOI：10.1021/jo00073a030

  日期：1993.10

  Acetylenic enol ether glycerides, 1 and 3, were found in the Okinawan marine sponge of the genus Petrosia. The plane structures of these glycerides were deduced from spectroscopic analysis. Their complete structures were established by enantioselective total synthesis of all possible stereoisomers using (R)-1-O-benzylglycerol and its (S)-enantiomer, prepared from D-mannitol and L-ascorbic acid, respectively, as chiral building blocks. The synthesis involves the palladium(O)-catalyzed coupling reaction of bromo enol ether 9 with enediyne 21 as a key step. It became evident from the synthesis that the natural product 1 consisted of a mixture of (7R,2'S)-24 (petrosyne Ia) and (7S,2S)-24 (petrosyne Ib), and the natural product 3 consisted of a mixture of (7R,2'S)-28 (petrosyne IIa) and (7S,2'S)-28 (petrosyne IIb).