ethyl 2-O-benzoyl-1-thio-β-D-glucopyranoside | 316352-73-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 2-O-benzoyl-1-thio-β-D-glucopyranoside
• 英文别名: thioethyl 2-O-benzoyl-β-D-glucopyranose；[(2S,3R,4S,5S,6R)-2-ethylsulfanyl-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl] benzoate
• CAS: 316352-73-5
• 化学式: C₁₅H₂₀O₆S
• 分子量: 328.386
• InChiKey: JGXIPCMZLURZDG-VVSAWPALSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  122
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  ethyl 2-O-benzoyl-1-thio-β-D-glucopyranoside 在 三氯化铝 、 硼烷-三甲胺络合物 、 sodium hydride 、 对甲苯磺酸 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 copper(l) chloride 作用下， 以 四氢呋喃 、 二氯甲烷 、 氯仿 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 生成 thioethyl 2-O-benzoyl-4-O-benzyl-3-O-isopropylcarbamoyl-β-D-glucopyranose
  参考文献：
  名称：

  Development of an Efficient, Regio- and Stereoselective Route to Libraries Based on the β-d-Glucose Scaffold

  摘要：

  The design and execution of an efficient synthetic route for the sequential functionalization of the five hydroxyl substituents. of beta -D-glucose has been achieved. This strategy, based on the stereoselective glycosidation of thioglycosides, provides a new approach for the parallel construction of a wide variety of beta -D-glucose analogues and as such holds promise for solid-support library syntheses.

  DOI：

  10.1021/jo001099v
• 作为产物：
  描述：

  3,4,6-tris-O-tert-butyldimethylsilyl-1,2-anhydro-α-D-glucopyranose 在 吡啶 、 四丁基氟化铵 、 三氟乙酸酐 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 204.0h， 生成 ethyl 2-O-benzoyl-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  Development of an Efficient, Regio- and Stereoselective Route to Libraries Based on the β-d-Glucose Scaffold

  摘要：

  The design and execution of an efficient synthetic route for the sequential functionalization of the five hydroxyl substituents. of beta -D-glucose has been achieved. This strategy, based on the stereoselective glycosidation of thioglycosides, provides a new approach for the parallel construction of a wide variety of beta -D-glucose analogues and as such holds promise for solid-support library syntheses.

  DOI：

  10.1021/jo001099v

文献信息

• Conformationally superarmed S-ethyl glycosyl donors as effective building blocks for chemoselective oligosaccharide synthesis in one pot
  作者：Mithila D. Bandara、Jagodige P. Yasomanee、Nigam P. Rath、Christian M. Pedersen、Mikael Bols、Alexei V. Demchenko

  DOI：10.1039/c6ob02498j

  日期：——

  superarmed glycosyl donors has been investigated. It was demonstrated that the S-ethyl leaving group allows for high reactivity, which is much higher than that of equally equipped S-phenyl glycosyl donors that were previously investigated by our groups. The superarmed S-ethyl glycosyl donors equipped with a 2-O-benzoyl group gave complete β-stereoselectivity. Utility of the new glycosyl donors has been

  已经研究了一系列新的超级糖基供体。结果表明，S-乙基离去基团具有高反应性，这比我们小组之前研究的同等装备的S-苯基糖基供体的反应性高得多。配备2- O-苯甲酰基的超级S-乙基糖基供体具有完全的β-立体选择性。新糖基供体的实用性已在所有反应组分从一开始就存在的一锅一加低聚糖合成中得到证实。
• Development of an Efficient, Regio- and Stereoselective Route to Libraries Based on the β-<scp>d</scp>-Glucose Scaffold
  作者：Ralph Hirschmann、Laurent Ducry、Amos B. Smith

  DOI：10.1021/jo001099v

  日期：2000.12.1

  The design and execution of an efficient synthetic route for the sequential functionalization of the five hydroxyl substituents. of beta -D-glucose has been achieved. This strategy, based on the stereoselective glycosidation of thioglycosides, provides a new approach for the parallel construction of a wide variety of beta -D-glucose analogues and as such holds promise for solid-support library syntheses.