thioethyl 3,4,6-tri-O-(tert-butyldimethylsilyl)-β-D-glucopyranose | 316352-68-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: thioethyl 3,4,6-tri-O-(tert-butyldimethylsilyl)-β-D-glucopyranose
• 英文别名: TBDMS(-3)[TBDMS(-4)][TBDMS(-6)]Glc(b)-SEt；(2S,3R,4R,5R,6R)-4,5-bis[[tert-butyl(dimethyl)silyl]oxy]-6-[[tert-butyl(dimethyl)silyl]oxymethyl]-2-ethylsulfanyloxan-3-ol
• CAS: 316352-68-8
• 化学式: C₂₆H₅₈O₅SSi₃
• 分子量: 567.066
• InChiKey: BIGMNKWHKQVPNP-JLMDMGSGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.63
• 重原子数：
  35
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  82.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  thioethyl 3,4,6-tri-O-(tert-butyldimethylsilyl)-β-D-glucopyranose 在 吡啶 、 三氯化铝 、 硼烷-三甲胺络合物 、 四丁基氟化铵 、 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 174.0h， 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 、 乙硫醇 在 三氟乙酸酐 作用下， 以 甲苯 为溶剂， 反应 48.0h， 以74%的产率得到thioethyl 3,4,6-tri-O-(tert-butyldimethylsilyl)-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.