(4S)-4-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxymethyl)-2,2-bis(trifluoromethyl)-1,3-oxazolidin-5-one | 231282-76-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (4S)-4-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxymethyl)-2,2-bis(trifluoromethyl)-1,3-oxazolidin-5-one
• 英文别名: [(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-[[(4S)-5-oxo-2,2-bis(trifluoromethyl)-1,3-oxazolidin-4-yl]methoxy]oxan-2-yl]methyl acetate
• CAS: 231282-76-1
• 化学式: C₂₀H₂₃F₆NO₁₂
• 分子量: 583.393
• InChiKey: QLHUBIJVLIFQLX-MCDJNTACSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  39
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  162
• 氢给体数：
  1
• 氢受体数：
  19

反应信息

• 作为反应物：
  描述：

  L-苯丙氨酰胺 、 (4S)-4-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxymethyl)-2,2-bis(trifluoromethyl)-1,3-oxazolidin-5-one 以 乙酸乙酯 为溶剂， 反应 3.0h， 以79%的产率得到O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)serylphenylalanine amide
  参考文献：
  名称：

  Hexafluoroacetone as Protecting and Activating Reagent: A New Approach to O-Glycosides

  摘要：

  O-Glycosylated hexafluoroacetone-protected amino acid derivatives have been synthesized starting from serine, threonine, 4-hydroxyproline and tyrosine. They represent a new class of building blocks suitable for a divergent approach to O-glycopeptides.

  DOI：

  10.3987/com-04-s(p)6
• 作为产物：
  描述：

  HFA-Ser 、 2,3,4,6-四乙酰氧基-alpha-D-吡喃葡萄糖溴化物 在 氰化汞 作用下， 以57%的产率得到(4S)-4-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxymethyl)-2,2-bis(trifluoromethyl)-1,3-oxazolidin-5-one
  参考文献：
  名称：

  A New Approach to Glycopeptides

  摘要：

  In only three or four steps glycosylated dipeptide and tripeptide fragments, respectively (see scheme), can be obtained from hydroxy amino acids by using a novel protecting group/activation concept. The method presented is even superior to the pentafluorophenyl ester method.

  DOI：

  10.1002/(sici)1521-3773(19990517)38:10<1414::aid-anie1414>3.0.co;2-l