(2S,3S,4S,5R,6R)-2-[3-(methyldisulfanyl)propoxy]-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxane | 1433190-77-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3S,4S,5R,6R)-2-[3-(methyldisulfanyl)propoxy]-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxane
• CAS: 1433190-77-2
• 化学式: C₃₈H₄₄O₆S₂
• 分子量: 660.896
• InChiKey: AGQCHBBLVBBWBN-DSVGPAFQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  46
• 可旋转键数：
  19
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.37
• 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：

  2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl thiol 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 51.25h， 生成 (2S,3S,4S,5R,6R)-2-[3-(methyldisulfanyl)propoxy]-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)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.