6,6′-di-O-docosanoyl-1-thio-α,α-D-trehalose | 1427716-49-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6,6′-di-O-docosanoyl-1-thio-α,α-D-trehalose
• 英文别名: [(2R,3S,4S,5R,6R)-6-[(2R,3R,4S,5S,6R)-6-(docosanoyloxymethyl)-3,4,5-trihydroxyoxan-2-yl]sulfanyl-3,4,5-trihydroxyoxan-2-yl]methyl docosanoate
• CAS: 1427716-49-1
• 化学式: C₅₆H₁₀₆O₁₂S
• 分子量: 1003.52
• InChiKey: HUPOIFATTKHFEL-LXOQPCSCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  17.8
• 重原子数：
  69
• 可旋转键数：
  48
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  218
• 氢给体数：
  6
• 氢受体数：
  13

反应信息

• 作为产物：
  描述：

  1-thio-α,α-trehalose 在 4-二甲氨基吡啶 、 溶剂黄146 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 、 二氯甲烷 、 丙酮 为溶剂， 反应 1.0h， 生成 6,6′-di-O-docosanoyl-1-thio-α,α-D-trehalose
  参考文献：
  名称：

  Synthesis of Thioglycoside Analogues of Maradolipid

  摘要：

  We describe here the first synthesis of thioglycoside analogues of maradolipid, based on a new procedure for the synthesis of 1-thiotrehalose developed recently in our laboratories. The challenging alpha,alpha-(1 -> 1') thioglycosidic linkage was constructed by Schmidt's inverse procedure in very high yield and excellent stereoselectivity. Subsequent protecting group manipulation and coupling with different fatty acids led smoothly to a group of symmetrical and unsymmetrical thiomaradolipids which would be of high value for biological studies.

  DOI：

  10.1021/jo400274s

文献信息

• Synthesis of Thioglycoside Analogues of Maradolipid
  作者：Xiaojun Zeng、Raymond Smith、Xiangming Zhu

  DOI：10.1021/jo400274s

  日期：2013.4.19

  We describe here the first synthesis of thioglycoside analogues of maradolipid, based on a new procedure for the synthesis of 1-thiotrehalose developed recently in our laboratories. The challenging alpha,alpha-(1 -> 1') thioglycosidic linkage was constructed by Schmidt's inverse procedure in very high yield and excellent stereoselectivity. Subsequent protecting group manipulation and coupling with different fatty acids led smoothly to a group of symmetrical and unsymmetrical thiomaradolipids which would be of high value for biological studies.