4-(((2S,3R,4S,5R,6R)-3,4,5-trimethoxy-6-(methoxymethyl)tetrahydro-2H-pyran-2-yl)thio)butan-1-ol | 1433190-17-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-(((2S,3R,4S,5R,6R)-3,4,5-trimethoxy-6-(methoxymethyl)tetrahydro-2H-pyran-2-yl)thio)butan-1-ol
• CAS: 1433190-17-0
• 化学式: C₁₄H₂₈O₆S
• 分子量: 324.439
• InChiKey: VSLJPVHVBOXEOX-RGDJUOJXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.91
• 重原子数：
  21.0
• 可旋转键数：
  10.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  66.38
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  2,3,4,6-tetra-O-methyl-1-deoxy-1-thio-β-D-glucopyranose 、 4-溴-1-丁醇 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以83%的产率得到4-(((2S,3R,4S,5R,6R)-3,4,5-trimethoxy-6-(methoxymethyl)tetrahydro-2H-pyran-2-yl)thio)butan-1-ol
  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