L-alanyl-O-(2-O-acetyl-α-D-galactopyranosyl)-L-threonyl-L-alanine | 766521-10-2

• 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: L-alanyl-O-(2-O-acetyl-α-D-galactopyranosyl)-L-threonyl-L-alanine
• CAS: 766521-10-2
• 化学式: C₁₈H₃₁N₃O₁₁
• 分子量: 465.458
• InChiKey: DMEJEICEWSMLIL-BZCUATRCSA-N

反应信息

• 作为产物：
  描述：

  N-(benzyloxycarbonyl)-L-alanyl-O-(2-O-acetyl-3-O-benzyl-4,6-O-benzylidene-α-D-galactopyranosyl)-L-threonyl-L-alanine benzyl ester 在 palladium on activated charcoal 氢气 、 溶剂黄146 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 以82%的产率得到L-alanyl-O-(2-O-acetyl-α-D-galactopyranosyl)-L-threonyl-L-alanine
  参考文献：
  名称：

  Sequential Glycoproteins:  Practical Method for the Synthesis of Antifreeze Glycoprotein Models Containing Base Labile Groups

  摘要：

  Practical and versatile methods for the preparation of glycopeptide polymers containing base labile moieties were established by use of 1-isobuthoxycarbonyl-2-isobuthoxy-1,2-dihydroquinoline (IIDQ) or 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride (DMT-MM) as polycondensation agents of glycopeptide units without any protection on the carbohydrate residues. These methods were applied for the synthesis of mucin-like glycoprotein mimics related to antifreeze glycoproteins (AFGPs), giving the target O-acetylated glycopolypeptides efficiently, while the conventional DPPA (diphenylphosphoryl azide) method gave complex mixtures of acyl migrated compounds.

  DOI：

  10.1021/ma049756z