(S)-(monomethoxytrityl)-1-mercaptopropan-3-ol | 189745-74-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: (S)-(monomethoxytrityl)-1-mercaptopropan-3-ol
• 英文别名: 1-Propanol, 3-[[(4-methoxyphenyl)diphenylmethyl]thio]-；3-[(4-methoxyphenyl)-diphenylmethyl]sulfanylpropan-1-ol
• CAS: 189745-74-2
• 化学式: C₂₃H₂₄O₂S
• 分子量: 364.508
• InChiKey: RRKAWXPIBDRKGU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  54.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-[(4-Methoxy-phenyl)-diphenyl-methylsulfanyl]-propionic acid methyl ester 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 (S)-(monomethoxytrityl)-1-mercaptopropan-3-ol
  参考文献：
  名称：

  Repetitive Solid Phase Glycosylation on an Alkyl Thiol Polymer Leading to Sugar Oligomers Containing 1,2-trans- and 1,2-cis-Glycosidic Linkages

  摘要：

  Repetitive solid phase glycosylation with sugar trichloroacetimidates is performed on an alkyl thiol polymer, demonstrating the selective formation of glycosidic bonds. The alpha-mannose and alpha-fucose linkages representing examples of 1,2-trans- and 1,2-cis-glycosides are synthesized. It is shown that the presented system can be operated in a cyclic manner, thus allowing many consecutive reaction steps to be performed on the solid support. Reaction conditions for solid phase glycosylation and deprotection are described. Analysis of all solid phase reactions is performed by MALDI-TOF mass spectrometry; the yield of solid phase glycosylation is quantitative up to the tetrameric stage judged from the mass spectra obtained from partial product cleavage after each reaction. Cleavage conditions for analysis and preparative isolation by thiophilic Lewis acids and oxidative methods are optimized.

  DOI：

  10.1021/jo970087f

文献信息

• Repetitive Solid Phase Glycosylation on an Alkyl Thiol Polymer Leading to Sugar Oligomers Containing 1,2-<i>trans</i>- and 1,2-<i>cis</i>-Glycosidic Linkages
  作者：Jörg Rademann、Richard R. Schmidt

  DOI：10.1021/jo970087f

  日期：1997.5.1

  Repetitive solid phase glycosylation with sugar trichloroacetimidates is performed on an alkyl thiol polymer, demonstrating the selective formation of glycosidic bonds. The alpha-mannose and alpha-fucose linkages representing examples of 1,2-trans- and 1,2-cis-glycosides are synthesized. It is shown that the presented system can be operated in a cyclic manner, thus allowing many consecutive reaction steps to be performed on the solid support. Reaction conditions for solid phase glycosylation and deprotection are described. Analysis of all solid phase reactions is performed by MALDI-TOF mass spectrometry; the yield of solid phase glycosylation is quantitative up to the tetrameric stage judged from the mass spectra obtained from partial product cleavage after each reaction. Cleavage conditions for analysis and preparative isolation by thiophilic Lewis acids and oxidative methods are optimized.