6,6′-di-O-(13-methylmyristyl)-2,3,4,2′,3′,4′-hexa-O-trimethylsilyl-1-thio-α,α-D-trehalose | 1427716-43-5

• 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-(13-methylmyristyl)-2,3,4,2′,3′,4′-hexa-O-trimethylsilyl-1-thio-α,α-D-trehalose
• 英文别名: [(2R,3R,4S,5R,6R)-6-[(2R,3R,4S,5R,6R)-6-(13-methyltetradecanoyloxymethyl)-3,4,5-tris(trimethylsilyloxy)oxan-2-yl]sulfanyl-3,4,5-tris(trimethylsilyloxy)oxan-2-yl]methyl 13-methyltetradecanoate
• CAS: 1427716-43-5
• 化学式: C₆₀H₁₂₆O₁₂SSi₆
• 分子量: 1240.23
• InChiKey: GHRRHLKQTUNMJA-QLDNUJHPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  17.47
• 重原子数：
  79
• 可旋转键数：
  44
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.97
• 拓扑面积：
  152
• 氢给体数：
  0
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  6,6′-di-O-(13-methylmyristyl)-2,3,4,2′,3′,4′-hexa-O-trimethylsilyl-1-thio-α,α-D-trehalose 在 Amberlite IR₁₂₀ (H+) resin 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 1.0h， 以93%的产率得到6,6′-di-O-(13-methylmyristyl)-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
• 作为产物：
  描述：

  2,3,4,6,2′,3′,4′,6′-octa-O-trimethylsilyl-1-thio-α,α-D-trehalose 在 4-二甲氨基吡啶 、 溶剂黄146 、 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， 生成 6,6′-di-O-(13-methylmyristyl)-2,3,4,2′,3′,4′-hexa-O-trimethylsilyl-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.