tert-butyldimethylsilyl 2-azido-6-O-benzyl-2-deoxy-3-O-levulinoyl-β-D-galactopyranoside | 1218904-34-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 糖脂
• 英文名称: tert-butyldimethylsilyl 2-azido-6-O-benzyl-2-deoxy-3-O-levulinoyl-β-D-galactopyranoside
• CAS: 1218904-34-7
• 化学式: C₂₄H₃₇N₃O₇Si
• 分子量: 507.659
• InChiKey: HKUTZJKASIZVMZ-IFPLKCGESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.27
• 重原子数：
  35.0
• 可旋转键数：
  11.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  140.05
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为产物：
  描述：

  tert-butyldimethylsilyl 2-azido-4,6-benzylidene-2-deoxy-3-O-levulinoyl-D-galactopyranoside 在 三乙基硅烷 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 tert-butyldimethylsilyl 2-azido-6-O-benzyl-2-deoxy-3-O-levulinoyl-α-D-galactopyranoside 、 tert-butyldimethylsilyl 2-azido-6-O-benzyl-2-deoxy-3-O-levulinoyl-β-D-galactopyranoside
  参考文献：
  名称：

  De Novo Synthesis of a 2-Acetamido-4-amino-2,4,6-trideoxy-d-galactose (AAT) Building Block for the Preparation of a Bacteroides fragilis A1 Polysaccharide Fragment

  摘要：

  Zwitterionic polysaccharides (ZPSs) are potent T-cell activators that naturally occur on the cell surface of bacteria and show potential as immunostimulatory agents. An unusual, yet important component of many ZPSs is 2-acetamido-4-amino-2,4,6-trideoxy-D-galactose (AAT). AAT building block 2 was prepared via a de novo synthesis from N-Cbz-L-threonine 5. Furthermore, building block 2 was used to synthesize disaccharide 15 that constitutes a fragment of zwitterionic polysaccharide A1 (PS A1) found in Bacteroides fragilis.

  DOI：

  10.1021/ol1003912