3-O-acetyl-2-azido-4-(benzyloxycarbonyl)amino-2,4,6-dideoxy-α-D-galactopyranosyl trichloroacetimidate | 145124-91-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-O-acetyl-2-azido-4-(benzyloxycarbonyl)amino-2,4,6-dideoxy-α-D-galactopyranosyl trichloroacetimidate
• 英文别名: O-(3-O-acetyl-2-azido-4-benzyloxycarbonylamino-2,4,6-trideoxy-α-D-galactopyranosyl) trichloroacetimidate
• CAS: 145124-91-0
• 化学式: C₁₈H₂₀Cl₃N₅O₆
• 分子量: 508.746
• InChiKey: MEZHOSCUYUUTBC-OBZOPLTCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.0
• 重原子数：
  32.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  155.7
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为产物：
  描述：

  、 三氯乙腈 在 potassium carbonate 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 生成 3-O-acetyl-2-azido-4-(benzyloxycarbonyl)amino-2,4,6-dideoxy-β-D-galactopyranosyl trichloroacetimidate 、 3-O-acetyl-2-azido-4-(benzyloxycarbonyl)amino-2,4,6-dideoxy-α-D-galactopyranosyl trichloroacetimidate
  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

文献信息

• Synthesis of the Core Structure of the Lipoteichoic Acid of<i>Streptococcus pneumoniae</i>
  作者：Christian Marcus Pedersen、Ignacio Figueroa‐Perez、Joshodeep Boruwa、Buko Lindner、Artur J. Ulmer、Ulrich Zähringer、Richard R. Schmidt

  DOI：10.1002/chem.201001204

  日期：2010.11.8

  Streptococcus pneumoniae LTA is a highly complex glycophospholipid that consists of nine carbohydrate residues: three glucose, two galactosamine and two 2‐acetamino‐4‐amino‐2,4,6‐trideoxygalactose (AATDgal) residues that are each differently linked, one ribitol and one diacylated glycerol (DAG) residue. Suitable building blocks for the glucose and the AATDgal residues were designed and their synthesis is described

  肺炎链球菌LTA是一种高度复杂的糖脂，由9个碳水化合物残基组成：3个葡萄糖，2个半乳糖胺和2个2-乙酰氨基-4-氨基-2,4,6-三乙氧基半乳糖（AATDgal）残基各有不同的连接方式，一个核糖醇和一个一个二酰基甘油（DAG）残基。设计了合适的葡萄糖和AATDgal残基的结构单元，并在本文中对其合成进行了描述。这些结构单元可以成功地合成核心结构Glcβ（1-3）AATDgalβ（1-3）Glcα（1- O）DAG，并以适当的保护形式进行进一步的扩链（1 b，1 c）和作为未保护的糖脂（1 a）用于生物学研究。这些研究表明1 a和1导致白介素8释放，但是不通过TLR2或TLR4作为受体。