p-methylphenyl 2,3-di-O-benzyl-4,6-O-p-chlorobenzylidene-thio-α-D-mannopyranoside | 952051-06-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-methylphenyl 2,3-di-O-benzyl-4,6-O-p-chlorobenzylidene-thio-α-D-mannopyranoside
• 英文别名: (2R,4aR,6R,7S,8S,8aR)-2-(4-chlorophenyl)-6-(4-methylphenyl)sulfanyl-7,8-bis(phenylmethoxy)-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxine
• CAS: 952051-06-8
• 化学式: C₃₄H₃₃ClO₅S
• 分子量: 589.152
• InChiKey: BXULJWOBZBOCAH-PBNHZRHQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  41
• 可旋转键数：
  9
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  71.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  p-methylphenyl 2,3-di-O-benzyl-4,6-O-p-chlorobenzylidene-thio-α-D-mannopyranoside 、 甲基 2,3-O-异亚丙基-alpha-L-吡喃鼠李糖苷 在 三氟甲磺酸 、 四丁基三氟甲磺酸铵 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以68%的产率得到methyl 2,3-di-O-benzyl-4,6-O-p-chlorobenzylidene-β-D-mannopyranosyl-(1-4)-2,3-O-isopropylidene-α-L-rhamnopyranoside
  参考文献：
  名称：

  Electrochemical Generation of Glycosyl Triflate Pools

  摘要：

  Glycosyl triflates, which serve as important intermediates in glycosylation reactions, were generated and accumulated by the low-temperature electrochemical oxidation of thioglycosides such as thioglucosides, thiogalactosides, and thiomannosides in the presence of tetrabutylammonium triflate (Bu-4-NOTf) as a supporting electrolyte. Thus-obtained solutions of glycosyl triflates (glycosyl triflate pools) were characterized by low-temperature NMR measurements. The thermal stability of glycosyl triflates and their reactions with glycosyl acceptors were also examined.

  DOI：

  10.1021/ja072440x
• 作为产物：
  描述：

  p-methylphenyl 4,6-O-p-chlorobenzylidene-thio-α-D-mannopyranoside 、 溴甲苯 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以84%的产率得到p-methylphenyl 2,3-di-O-benzyl-4,6-O-p-chlorobenzylidene-thio-α-D-mannopyranoside
  参考文献：
  名称：

  Electrochemical Generation of Glycosyl Triflate Pools

  摘要：

  Glycosyl triflates, which serve as important intermediates in glycosylation reactions, were generated and accumulated by the low-temperature electrochemical oxidation of thioglycosides such as thioglucosides, thiogalactosides, and thiomannosides in the presence of tetrabutylammonium triflate (Bu-4-NOTf) as a supporting electrolyte. Thus-obtained solutions of glycosyl triflates (glycosyl triflate pools) were characterized by low-temperature NMR measurements. The thermal stability of glycosyl triflates and their reactions with glycosyl acceptors were also examined.

  DOI：

  10.1021/ja072440x

文献信息

• Electrochemical Generation of Glycosyl Triflate Pools
  作者：Toshiki Nokami、Akito Shibuya、Hiroaki Tsuyama、Seiji Suga、Albert A. Bowers、David Crich、Jun-ichi Yoshida

  DOI：10.1021/ja072440x

  日期：2007.9.1

  Glycosyl triflates, which serve as important intermediates in glycosylation reactions, were generated and accumulated by the low-temperature electrochemical oxidation of thioglycosides such as thioglucosides, thiogalactosides, and thiomannosides in the presence of tetrabutylammonium triflate (Bu-4-NOTf) as a supporting electrolyte. Thus-obtained solutions of glycosyl triflates (glycosyl triflate pools) were characterized by low-temperature NMR measurements. The thermal stability of glycosyl triflates and their reactions with glycosyl acceptors were also examined.