(2R,3R,4S,5R,6R)-3,4,5-trimethoxy-2-(methoxymethyl)-6-[4-(methyldisulfanyl)butoxy]oxane | 1433190-65-8

• 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: (2R,3R,4S,5R,6R)-3,4,5-trimethoxy-2-(methoxymethyl)-6-[4-(methyldisulfanyl)butoxy]oxane
• CAS: 1433190-65-8
• 化学式: C₁₅H₃₀O₆S₂
• 分子量: 370.532
• InChiKey: FGVHYOCKVJFHRV-UXXRCYHCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  23
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  106
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  4-(((2S,3R,4S,5R,6R)-3,4,5-trimethoxy-6-(methoxymethyl)tetrahydro-2H-pyran-2-yl)thio)butan-1-ol 、 dimethyl(methylthio)sulfonium tetrafluoroborate 反应 48.25h， 以49%的产率得到(2R,3R,4S,5R,6R)-3,4,5-trimethoxy-2-(methoxymethyl)-6-[4-(methyldisulfanyl)butoxy]oxane
  参考文献：
  名称：

  Exploring the Native Chemical Ligation Concept for Highly Stereospecific Glycosylation Reactions

  摘要：

  Various O-alkyl glycosides were obtained in a highly stereospecific manner with retention of configuration at the anomeric center. Our method has customized native chemical ligation concept for glycoconjugates synthesis, utilizing a meticulously controlled activating system. To explain the origin of stereoselective preference, an S(N)i mechanism was proposed and corroborated by computational calculations.

  DOI：

  10.1021/jo400020q

文献信息

• Exploring the Native Chemical Ligation Concept for Highly Stereospecific Glycosylation Reactions
  作者：Kim Le Mai Hoang、Yaguang Bai、Xin Ge、Xue-Wei Liu

  DOI：10.1021/jo400020q

  日期：2013.6.7

  Various O-alkyl glycosides were obtained in a highly stereospecific manner with retention of configuration at the anomeric center. Our method has customized native chemical ligation concept for glycoconjugates synthesis, utilizing a meticulously controlled activating system. To explain the origin of stereoselective preference, an S(N)i mechanism was proposed and corroborated by computational calculations.