1,5-anhydro-6-O-tert-butyldiphenylsilyl-3,4-O-isopropylidene-D-galactitol | 1170714-31-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧吡喃
• 英文名称: 1,5-anhydro-6-O-tert-butyldiphenylsilyl-3,4-O-isopropylidene-D-galactitol
• 英文别名: (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-ol
• CAS: 1170714-31-4
• 化学式: C₂₅H₃₄O₅Si
• 分子量: 442.627
• InChiKey: WQPHHRFFOFZPPR-AFXVXQJMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.84
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1,5-anhydro-6-O-tert-butyldiphenylsilyl-3,4-O-isopropylidene-D-galactitol 、 benzyl (2S)-1-benzyloxycarbonylaziridin-2-carboxylate 在 三氟化硼乙醚 作用下， 以 氯仿 为溶剂， 反应 16.0h， 以54%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 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
• 作为产物：
  描述：

  1,5-anhydro-6-O-tert-butyldiphenylsilyl-D-galactitol 、 2,2-二甲氧基丙烷 在 对甲苯磺酸 作用下， 以 丙酮 为溶剂， 反应 1.0h， 以78%的产率得到1,5-anhydro-6-O-tert-butyldiphenylsilyl-3,4-O-isopropylidene-D-galactitol
  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.