tert-butyldimethylsilyl 2-azido-6-O-benzyl-2-deoxy-3-O-fluorenylmethoxycarbonyl-β-D-galactopyranoside | 1218904-35-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: tert-butyldimethylsilyl 2-azido-6-O-benzyl-2-deoxy-3-O-fluorenylmethoxycarbonyl-β-D-galactopyranoside
• CAS: 1218904-35-8
• 化学式: C₃₄H₄₁N₃O₇Si
• 分子量: 631.801
• InChiKey: FNAMNSPQVAIAAY-VJLURNNQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.32
• 重原子数：
  45.0
• 可旋转键数：
  10.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  132.21
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  3-O-acetyl-2-azido-4-(benzyloxycarbonyl)amino-2,4,6-dideoxy-D-galactopyranosyl N-phenyltrifluoroacetimidate 、 tert-butyldimethylsilyl 2-azido-6-O-benzyl-2-deoxy-3-O-fluorenylmethoxycarbonyl-β-D-galactopyranoside 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以59%的产率得到[(2R,3R,4S,5S,6R)-3-azido-2-[(2R,3R,4R,5R,6S)-5-azido-6-[tert-butyl(dimethyl)silyl]oxy-4-(9H-fluoren-9-ylmethoxycarbonyloxy)-2-(phenylmethoxymethyl)oxan-3-yl]oxy-6-methyl-5-(phenylmethoxycarbonylamino)oxan-4-yl] acetate
  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
• 作为产物：
  描述：

  tert-butyldimethylsilyl 2-azido-4,6-benzylidene-2-deoxy-3-O-fluorenylmethoxycarbonyl-β-D-galactopyranoside 在 三乙基硅烷 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 以61%的产率得到tert-butyldimethylsilyl 2-azido-6-O-benzyl-2-deoxy-3-O-fluorenylmethoxycarbonyl-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