benzyl S-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-galactopyranosyl)-(1->4)-2,3-di-O-acetyl-4-deoxy-6-(4-methoxybenzyl)-4-thio-β-D-glucopyranoside | 681485-06-3

• 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-6-(4-methoxybenzyl)-4-thio-β-D-glucopyranoside
• CAS: 681485-06-3
• 化学式: C₃₉H₄₉NO₁₆S
• 分子量: 819.881
• InChiKey: JAYZOHUMDKZMEG-GNXZURMGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.77
• 重原子数：
  57.0
• 可旋转键数：
  17.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  206.75
• 氢给体数：
  1.0
• 氢受体数：
  17.0

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-6-(4-methoxybenzyl)-4-thio-β-D-glucopyranoside 在 jones reagent 、 sodium methylate 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 、 丙酮 为溶剂， 反应 1.33h， 生成 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：

  2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-1-thio-β-D-galactopyranose 、 benzyl 2,3-di-O-acetyl-6-O-para-methoxybenzyl-4-O-trifluoromethanesulfonyl-β-D-galactopyranoside 在 sodium hydride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以43%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-6-(4-methoxybenzyl)-4-thio-β-D-glucopyranoside
  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