benzyl S-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-galactopyranosyl)-(1->4)-2,3-di-O-acetyl-4-deoxy-4-thio-β-D-glucopyranosiduronic acid | 681485-08-5

• 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: benzyl S-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-galactopyranosyl)-(1->4)-2,3-di-O-acetyl-4-deoxy-4-thio-β-D-glucopyranosiduronic acid
• CAS: 681485-08-5
• 化学式: C₃₁H₃₉NO₁₆S
• 分子量: 713.714
• InChiKey: XRFJRGPKHGAREH-XRMRJVAGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.63
• 重原子数：
  49.0
• 可旋转键数：
  13.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  225.59
• 氢给体数：
  2.0
• 氢受体数：
  16.0

反应信息

• 作为反应物：
  描述：

  benzyl S-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-galactopyranosyl)-(1->4)-2,3-di-O-acetyl-4-deoxy-4-thio-β-D-glucopyranosiduronic acid 在 sodium methylate 作用下， 以 甲醇 为溶剂， 以48%的产率得到benzyl S-(2-acetamido-2-deoxy-β-D-galactopyranosyl)-(1->4)-4-deoxy-4-thio-β-D-glucopyranosiduronic acid
  参考文献：
  名称：

  The synthesis of a novel thio-linked disaccharide of chondroitin as a potential inhibitor of polysaccharide lyases

  摘要：

  A thio-linked disaccharide based on the structure of the glycosaminoglycan chondroitin was synthesized as a potential inhibitor of chondroitin AC lyase from Flavobacterium heparinum for structural analysis of the active site. Instead it was found to be a slow substrate, thereby demonstrating that lyases, in contrast to glycosidases, can cleave thioglycoside links between sugars. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2003.12.011
• 作为产物：
  描述：

  benzyl S-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-galactopyranosyl)-(1->4)-2,3-di-O-acetyl-4-deoxy-4-thio-β-D-glucopyranoside 在 jones reagent 作用下， 以 丙酮 为溶剂， 反应 1.0h， 以73%的产率得到benzyl S-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-galactopyranosyl)-(1->4)-2,3-di-O-acetyl-4-deoxy-4-thio-β-D-glucopyranosiduronic acid
  参考文献：
  名称：

  The synthesis of a novel thio-linked disaccharide of chondroitin as a potential inhibitor of polysaccharide lyases

  摘要：

  A thio-linked disaccharide based on the structure of the glycosaminoglycan chondroitin was synthesized as a potential inhibitor of chondroitin AC lyase from Flavobacterium heparinum for structural analysis of the active site. Instead it was found to be a slow substrate, thereby demonstrating that lyases, in contrast to glycosidases, can cleave thioglycoside links between sugars. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2003.12.011