carboxymethyl-3,4,6-O-benzyl-2-O-[2-O-(2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-3,4,6-tri-O-benzyl-α-D-mannopyranosyl]-α-D-mannopyranoside | 1240795-21-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: carboxymethyl-3,4,6-O-benzyl-2-O-[2-O-(2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-3,4,6-tri-O-benzyl-α-D-mannopyranosyl]-α-D-mannopyranoside
• CAS: 1240795-21-4
• 化学式: C₈₅H₉₀O₁₉
• 分子量: 1415.64
• InChiKey: OHSPRBKEGYXCLV-FPYWAGPVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.13
• 重原子数：
  104.0
• 可旋转键数：
  38.0
• 环数：
  12.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  202.05
• 氢给体数：
  1.0
• 氢受体数：
  18.0

反应信息

• 作为反应物：
  描述：

  carboxymethyl-3,4,6-O-benzyl-2-O-[2-O-(2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-3,4,6-tri-O-benzyl-α-D-mannopyranosyl]-α-D-mannopyranoside 在 氨 、 sodium 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 以72%的产率得到carboxymethyl-2-O-[(2-O-α-D-mannopyranosyl)-α-D-mannopyranosyl]-α-D-mannopyranoside
  参考文献：
  名称：

  Synthesis of Multivalent Tuberculosis and Leishmania-Associated Capping Carbohydrates Reveals Structure-Dependent Responses Allowing Immune Evasion

  摘要：

  Mycobacterium tuberculosis and the protozoan parasites of the genus Leishmania are intracellular pathogens that can survive in macrophages-the very white blood cells of the immune system responsible for engulfing and ultimately clearing foreign invaders. The ability of these pathogens to hide within immune cells has made the design of effective therapies, including vaccines, to control tuberculosis and leishmaniasis particularly challenging. Herein we present the synthesis and development of carbohydrate-based probes to demonstrate that changes in pathogen-associated surface oligosaccharides are sufficient to alter cellular immune responses and thereby let a pathogen hide from immune surveillance.

  DOI：

  10.1021/ja103351m
• 作为产物：
  描述：

  3-(perfluorooctyl)propanyloxybutenyl-3,4,6-O-benzyl-2-O-[2-O-(2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-3,4,6-tri-O-benzyl-α-D-mannopyranosyl]-α-D-mannopyranoside 在 臭氧 、 三苯基膦 、 Jones reagent 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 1.08h， 以87%的产率得到carboxymethyl-3,4,6-O-benzyl-2-O-[2-O-(2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-3,4,6-tri-O-benzyl-α-D-mannopyranosyl]-α-D-mannopyranoside
  参考文献：
  名称：

  Synthesis of Multivalent Tuberculosis and Leishmania-Associated Capping Carbohydrates Reveals Structure-Dependent Responses Allowing Immune Evasion

  摘要：

  Mycobacterium tuberculosis and the protozoan parasites of the genus Leishmania are intracellular pathogens that can survive in macrophages-the very white blood cells of the immune system responsible for engulfing and ultimately clearing foreign invaders. The ability of these pathogens to hide within immune cells has made the design of effective therapies, including vaccines, to control tuberculosis and leishmaniasis particularly challenging. Herein we present the synthesis and development of carbohydrate-based probes to demonstrate that changes in pathogen-associated surface oligosaccharides are sufficient to alter cellular immune responses and thereby let a pathogen hide from immune surveillance.

  DOI：

  10.1021/ja103351m