pent-4'-enyl 2-azido-4,6-O-benzylidene-2-deoxy-1-thio-β-D-galactopyranoside | 191341-71-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: pent-4'-enyl 2-azido-4,6-O-benzylidene-2-deoxy-1-thio-β-D-galactopyranoside
• CAS: 191341-71-6
• 化学式: C₁₈H₂₃N₃O₄S
• 分子量: 377.464
• InChiKey: RYOIJMIJQFLSTM-ZXLDYLNASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.56
• 重原子数：
  26.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  96.68
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  pent-4'-enyl 2-azido-4,6-O-benzylidene-2-deoxy-1-thio-β-D-galactopyranoside 、 2,3,4,6-四乙酰氧基-alpha-D-吡喃糖溴化物 在 4 A molecular sieve 、 silver trifluoromethanesulfonate 作用下， 生成 pent-4'-enyl 3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-2-azido-4,6-O-benzylidene-2-deoxy-1-thio-β-D-galactopyranoside 、 pent-4'-enyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-galactopyranoside
  参考文献：
  名称：

  Synthesis of TN and T Antigen Glycopeptide Sequences of tumor-associated MUC-1 usingS-pent-4-enyl thioglycosides

  摘要：

  The syntheses of glycopeptides 34 and 38 with tumor associated T-N and T antigen structure containing a partial sequence of the tandem repeat unit of the polymorphic epithelial mucin MUC-1 were achieved via fragment condensations. Electrophilic activation of S-pent-4-enyl thioglycosides was applied for the construction of O-glycosyl amino acid and saccharide building blocks.

  DOI：

  10.1002/prac.19973390160
• 作为产物：
  描述：

  [(2R,3R,4R,5R,6S)-3,4-diacetyloxy-5-azido-6-pent-4-enoxycarbothioylsulfanyloxan-2-yl]methyl acetate 在 sodium methylate 、 对甲苯磺酸 、 sodium iodide 作用下， 以 甲醇 、 丙酮 、 乙腈 为溶剂， 反应 18.0h， 生成 pent-4'-enyl 2-azido-4,6-O-benzylidene-2-deoxy-1-thio-β-D-galactopyranoside
  参考文献：
  名称：

  Synthesis of TN and T Antigen Glycopeptide Sequences of tumor-associated MUC-1 usingS-pent-4-enyl thioglycosides

  摘要：

  The syntheses of glycopeptides 34 and 38 with tumor associated T-N and T antigen structure containing a partial sequence of the tandem repeat unit of the polymorphic epithelial mucin MUC-1 were achieved via fragment condensations. Electrophilic activation of S-pent-4-enyl thioglycosides was applied for the construction of O-glycosyl amino acid and saccharide building blocks.

  DOI：

  10.1002/prac.19973390160