Nα-(fluoren-9-ylmethoxycarbonyl)-3-O-[1,5-anhydro-6-O-tert-butyldiphenylsilyl-3,4-O-isopropylidene-D-galactitol-2-yl]-L-threonine | 1170714-44-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: Nα-(fluoren-9-ylmethoxycarbonyl)-3-O-[1,5-anhydro-6-O-tert-butyldiphenylsilyl-3,4-O-isopropylidene-D-galactitol-2-yl]-L-threonine
• CAS: 1170714-44-9
• 化学式: C₄₄H₅₁NO₉Si
• 分子量: 765.976
• InChiKey: RREIUSDGZZYNTD-NJOLGPTOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.25
• 重原子数：
  55.0
• 可旋转键数：
  12.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  121.78
• 氢给体数：
  2.0
• 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-threonine 、 9-芴甲基-N-琥珀酰亚胺基碳酸酯 在 碳酸氢钠 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 以83%的产率得到Nα-(fluoren-9-ylmethoxycarbonyl)-3-O-[1,5-anhydro-6-O-tert-butyldiphenylsilyl-3,4-O-isopropylidene-D-galactitol-2-yl]-L-threonine
  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