O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-L-threonyl-L-phenylalanine amide | 231282-81-8

• 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: O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-L-threonyl-L-phenylalanine amide
• 英文别名: O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)threonylphenylalanine amide；[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-[(2R,3S)-3-amino-4-[[(2S)-1-amino-1-oxo-3-phenylpropan-2-yl]amino]-4-oxobutan-2-yl]oxyoxan-2-yl]methyl acetate
• CAS: 231282-81-8
• 化学式: C₂₇H₃₇N₃O₁₂
• 分子量: 595.604
• InChiKey: OZYCFQPFAVSJQP-RFLMMLQASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  42
• 可旋转键数：
  17
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  222
• 氢给体数：
  3
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  苄氧羰基-L-丙氨酸 、 O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-L-threonyl-L-phenylalanine amide 在 N-羟基-7-氮杂苯并三氮唑 、 达卡巴嗪 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以73%的产率得到Z-Ala-Thr(TAcGlc)-Phe-NH2
  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：

  2,3,4,6-四-O-乙酰基-Β-D-吡喃半乳糖酰基-2,2,2-三氯代亚氨乙酸酯 在 三氟化硼乙醚 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 73.0h， 生成 O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-L-threonyl-L-phenylalanine 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

文献信息

• A New Approach to Glycopeptides
  作者：Klaus Burger、Michael Kluge、Susanna Fehn、Beate Koksch、Lothar Hennig、Gerhard Müller

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

  日期：1999.5.17

  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.
• Hexafluoroacetone as Protecting and Activating Reagent: A New Approach to O-Glycosides
  作者：Klaus Burger、Michael Kluge、Beate Koksch、Susanna Fehn、Christoph Böttcher、Lothar Hennig、Gerhard Müller

  DOI：10.3987/com-04-s(p)6

  日期：——

  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.