Nα-benzyloxycarbonyl-3-O-[1,5-anhydro-6-O-tert-butyldiphenylsilyl-3,4-O-isopropylidene-D-galactitol-2-yl]-L-threonine benzyl ester | 1170714-35-8

• 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: Nα-benzyloxycarbonyl-3-O-[1,5-anhydro-6-O-tert-butyldiphenylsilyl-3,4-O-isopropylidene-D-galactitol-2-yl]-L-threonine benzyl ester
• 英文别名: benzyl (2S,3R)-3-[[(3aS,4R,7S,7aR)-4-[[tert-butyl(diphenyl)silyl]oxymethyl]-2,2-dimethyl-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-7-yl]oxy]-2-(phenylmethoxycarbonylamino)butanoate
• CAS: 1170714-35-8
• 化学式: C₄₄H₅₃NO₉Si
• 分子量: 767.992
• InChiKey: NPWUFCTXOWFTQT-OZBZQVSWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.29
• 重原子数：
  55
• 可旋转键数：
  17
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  111
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  Nα-benzyloxycarbonyl-3-O-[1,5-anhydro-6-O-tert-butyldiphenylsilyl-3,4-O-isopropylidene-D-galactitol-2-yl]-L-threonine benzyl ester 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 反应 48.0h， 以95%的产率得到Nα-benzyloxycarbonyl-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
• 作为产物：
  描述：

  1,5-anhydro-6-O-tert-butyldiphenylsilyl-3,4-O-isopropylidene-D-galactitol 、 benzyl (2S,3S)-1-benzyloxycarbonyl-3-methyl-2-aziridinecarboxylate 在 三氟化硼乙醚 作用下， 以 氯仿 为溶剂， 反应 16.0h， 以44%的产率得到Nα-benzyloxycarbonyl-3-O-[1,5-anhydro-6-O-tert-butyldiphenylsilyl-3,4-O-isopropylidene-D-galactitol-2-yl]-L-threonine benzyl ester
  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

文献信息

• Aziridine ring opening as regio- and stereoselective access to O-glycosyl amino acids and their transformation into O-glycopeptide mimetics
  作者：Andreas Schäfer、Dirk Henkensmeier、Lars Kröger、Joachim Thiem

  DOI：10.1016/j.tetasy.2009.02.038

  日期：2009.5

  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.