3-O-[1,5-anhydro-D-galactitol-2-yl]-L-serine trifluoroacetate | 1170714-39-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-O-[1,5-anhydro-D-galactitol-2-yl]-L-serine trifluoroacetate
• CAS: 1170714-39-2
• 化学式: C₂HF₃O₂*C₉H₁₇NO₇
• 分子量: 365.26
• InChiKey: GDFCWAIQPWNASU-VGXOUZMMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.47
• 重原子数：
  24.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  179.77
• 氢给体数：
  6.0
• 氢受体数：
  8.0

反应信息

• 作为产物：
  描述：

  Nα-benzyloxycarbonyl-3-O-[1,5-anhydro-6-O-tert-butyldiphenylsilyl-3,4-O-isopropylidene-D-galactitol-2-yl]-L-serine 、 三氟乙酸 反应 1.0h， 以86%的产率得到3-O-[1,5-anhydro-D-galactitol-2-yl]-L-serine trifluoroacetate
  参考文献：
  名称：

  Aziridine ring opening as regio- and stereoselective access to O-glycosyl amino acids and their transformation into O-glycopeptide mimetics

  摘要：

  Glycosyl amino acid mimetics of the typical GalNAc-(1 -> O)-Ser/Thr motif of O-glycopeptides were synthesised. Starting from galactose a 1,5-anhydro derivative could be obtained and regio- and stereoselectively coupled to serine- or threonine-derived aziridine compounds, respectively. The corresponding Fmoc derivatives could be used to prepare two 13-mer glycopeptides of the mucin MUC1 carrying instead of Ser-2 or Th-5, the corresponding O-glcycosyl amino acid mimetics. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.02.038