thioethyl 3,4-di-O-benzyl-6-O-4'-oxo-5'-phenyl-valeryl-2-pivaloyl-β-D-glucopyranoside | 449777-93-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: thioethyl 3,4-di-O-benzyl-6-O-4'-oxo-5'-phenyl-valeryl-2-pivaloyl-β-D-glucopyranoside
• CAS: 449777-93-9
• 化学式: C₃₈H₄₆O₈S
• 分子量: 662.844
• InChiKey: BPQRAPJFYISRGX-BOYYEFAASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.73
• 重原子数：
  47.0
• 可旋转键数：
  16.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  97.36
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  thioethyl 3,4-di-O-benzyl-6-O-4'-oxo-5'-phenyl-valeryl-2-pivaloyl-β-D-glucopyranoside 在 N-溴代丁二酰亚胺(NBS) 、 三氟甲磺酸三甲基硅酯 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 13.0h， 生成 4-Oxo-5-phenyl-pentanoic acid (2R,3R,4S,5R,6R)-3,4-bis-benzyloxy-5-(2,2-dimethyl-propionyloxy)-6-((3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-ylmethoxy)-tetrahydro-pyran-2-ylmethyl ester
  参考文献：
  名称：

  Linker Influence on the Stereochemical Outcome of Glycosylations Utilizing Solid Support-Bound Glycosyl Phosphates

  摘要：

  [GRAPHICS]Glycosyl phosphates can be readily accessed on a solid support via a three-step procedure from support-bound glycals. These resin-bound glycosyl phosphates were successfully used as glycosylating agents for coupling with a series of nucleophiles. The stereochemical outcome of disaccharide formation was dependent on the nature of the linker connecting the saccharide to the polymer. Interestingly, other glycosyl donors such as thioglycosides and trichloroacetimidates did not exhibit such a dependence, indicating a different reaction mechanism for glycosylation.

  DOI：

  10.1021/ol026276o
• 作为产物：
  描述：

  6-O-(三异丙基硅基)-D-葡萄烯糖 在 4-二甲氨基吡啶 、 四丁基氟化铵 、 二甲基二环氧乙烷 、 sodium hydride 、 溶剂黄146 、 N,N'-二环己基碳二亚胺 、 三氟乙酸酐 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 30.25h， 生成 thioethyl 3,4-di-O-benzyl-6-O-4'-oxo-5'-phenyl-valeryl-2-pivaloyl-β-D-glucopyranoside
  参考文献：
  名称：

  Linker Influence on the Stereochemical Outcome of Glycosylations Utilizing Solid Support-Bound Glycosyl Phosphates

  摘要：

  [GRAPHICS]Glycosyl phosphates can be readily accessed on a solid support via a three-step procedure from support-bound glycals. These resin-bound glycosyl phosphates were successfully used as glycosylating agents for coupling with a series of nucleophiles. The stereochemical outcome of disaccharide formation was dependent on the nature of the linker connecting the saccharide to the polymer. Interestingly, other glycosyl donors such as thioglycosides and trichloroacetimidates did not exhibit such a dependence, indicating a different reaction mechanism for glycosylation.

  DOI：

  10.1021/ol026276o