[(2R,3R,4R,5R,6S)-3,4-diacetyloxy-5-azido-6-pent-4-enoxycarbothioylsulfanyloxan-2-yl]methyl acetate | 191341-66-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(2R,3R,4R,5R,6S)-3,4-diacetyloxy-5-azido-6-pent-4-enoxycarbothioylsulfanyloxan-2-yl]methyl acetate
• CAS: 191341-66-9
• 化学式: C₁₈H₂₅N₃O₈S₂
• 分子量: 475.544
• InChiKey: QHOOGFGFUYNFMS-UUAJXVIYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  31
• 可旋转键数：
  15
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  169
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  [(2R,3R,4R,5R,6S)-3,4-diacetyloxy-5-azido-6-pent-4-enoxycarbothioylsulfanyloxan-2-yl]methyl acetate 在 sodium methylate 、 sodium iodide 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 17.5h， 生成 (2R,3R,4R,5R,6S)-5-Azido-2-hydroxymethyl-6-pent-4-enylsulfanyl-tetrahydro-pyran-3,4-diol
  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：

  peracetylated α-glycosyl nitrate 2-azido-2-deoxy-D-galactopyranose 、 potassium O-(pent-4-en-1-yl)methioate 在 18-冠醚-6 作用下， 以 二氯甲烷 为溶剂， 反应 50.0h， 以55%的产率得到[(2R,3R,4R,5R,6S)-3,4-diacetyloxy-5-azido-6-pent-4-enoxycarbothioylsulfanyloxan-2-yl]methyl acetate
  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