(3R)-1-[1-(methoxycarbonyl)isopropyl]-3-(2-nitrobenzenesulfonamino)-3-[1-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-1,2,3-triazol-4-ylmethyl]-azetidin-2-one | 1029899-21-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (3R)-1-[1-(methoxycarbonyl)isopropyl]-3-(2-nitrobenzenesulfonamino)-3-[1-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-1,2,3-triazol-4-ylmethyl]-azetidin-2-one
• CAS: 1029899-21-5
• 化学式: C₃₁H₃₈N₆O₁₆S
• 分子量: 782.739
• InChiKey: YINZXILYPCUYJH-SKXMKSBUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  54.0
• 可旋转键数：
  14.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  281.06
• 氢给体数：
  1.0
• 氢受体数：
  19.0

反应信息

• 作为反应物：
  描述：

  (3R)-1-[1-(methoxycarbonyl)isopropyl]-3-(2-nitrobenzenesulfonamino)-3-[1-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-1,2,3-triazol-4-ylmethyl]-azetidin-2-one 、 4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-十七氟十一酰氯 在 potassium carbonate 、 苯硫酚 作用下， 以 乙腈 为溶剂， 反应 1.0h， 以55%的产率得到(3R)-1-[1-(methoxycarbonyl)isopropyl]-3-(2H,2H,3H,3H-perfluoroundecanamido)-3-[1-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-1,2,3-triazol-4-yl-methyl]-azetidin-2-one
  参考文献：
  名称：

  “Click” Saccharide/β-Lactam Hybrids for Lectin Inhibition

  摘要：

  Hybrid glycopeptide beta-lactam mimetics designed to bind lectins or carbohydrate recognition domains in selectins have been prepared according to a "shape-modulating linker" design. This approach was implemented using the azide-alkyne "click" cycloaddition reaction, and as shown by NMR/MD experiments, binding of the resulting mimetics to Ulex Europaeus Lectin-1 (UEL-1) occurred after a "bent-to-extended" conformational change around a partially rotatable triazolylmethylene moiety.

  DOI：

  10.1021/ol8006259
• 作为产物：
  描述：

  2,3,4,6-四-O-乙酰基-α-D-叠氮化吡喃甘露糖 、 (3R)-3-(propargyl)-1-[1-(methoxycarbonyl)-isopropyl]-3-(2-nitrobenzenesulfonamino)-azetidin-2-one 在 copper(II) sulfate 、 sodium ascorbate 作用下， 以 四氢呋喃 、 水 、 叔丁醇 为溶剂， 以90%的产率得到(3R)-1-[1-(methoxycarbonyl)isopropyl]-3-(2-nitrobenzenesulfonamino)-3-[1-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-1,2,3-triazol-4-ylmethyl]-azetidin-2-one
  参考文献：
  名称：

  “Click” Saccharide/β-Lactam Hybrids for Lectin Inhibition

  摘要：

  Hybrid glycopeptide beta-lactam mimetics designed to bind lectins or carbohydrate recognition domains in selectins have been prepared according to a "shape-modulating linker" design. This approach was implemented using the azide-alkyne "click" cycloaddition reaction, and as shown by NMR/MD experiments, binding of the resulting mimetics to Ulex Europaeus Lectin-1 (UEL-1) occurred after a "bent-to-extended" conformational change around a partially rotatable triazolylmethylene moiety.

  DOI：

  10.1021/ol8006259