thioethyl 2-O-benzylcarbamoyl-4,6-O-(4-methoxybenzylidene)-β-D-glucopyranose | 316353-12-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: thioethyl 2-O-benzylcarbamoyl-4,6-O-(4-methoxybenzylidene)-β-D-glucopyranose
• 英文别名: [(4aR,6S,7R,8S,8aS)-6-ethylsulfanyl-8-hydroxy-2-(4-methoxyphenyl)-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-7-yl] N-benzylcarbamate
• CAS: 316353-12-5
• 化学式: C₂₄H₂₉NO₇S
• 分子量: 475.563
• InChiKey: ZDZWSGIWAIDGRA-VGPVBAISSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  33
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  121
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  thioethyl 2-O-benzylcarbamoyl-4,6-O-(4-methoxybenzylidene)-β-D-glucopyranose 在 N-碘代丁二酰亚胺 、 三氟甲磺酸 、 硼烷-三甲胺络合物 、 potassium carbonate 、 copper(l) chloride 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 31.5h， 生成 2-(morpholin-4-yl)ethyl 2-O-benzylcarbamoyl-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 、 氢氟酸 、 对甲苯磺酸 、 三氟乙酸酐 作用下， 以 二氯甲烷 、 氯仿 、 甲苯 、 乙腈 为溶剂， 反应 174.0h， 生成 thioethyl 2-O-benzylcarbamoyl-4,6-O-(4-methoxybenzylidene)-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

文献信息

• 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.