Nα-benzyloxycarbonyl-3-O-[1,5-anhydro-6-O-tert-butyldiphenylsilyl-3,4-O-isopropylidene-D-galactitol-2-yl]-L-serine | 1170714-36-9

• 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-serine
• 英文别名: (2S)-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-aminopropanoic acid
• CAS: 1170714-36-9
• 化学式: C₂₈H₃₉NO₇Si
• 分子量: 529.706
• InChiKey: KOZCYTAFOKQFPQ-LJXDPWEESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.28
• 重原子数：
  37
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  110
• 氢给体数：
  2
• 氢受体数：
  8

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-serine 、 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99%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-serine
  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：

  Nα-benzyloxycarbonyl-3-O-[1,5-anhydro-6-O-tert-butyldiphenylsilyl-3,4-O-isopropylidene-D-galactitol-2-yl]-L-serine benzyl ester 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 反应 48.0h， 以91%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-serine
  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