benzyl N-benzyloxycarbonyl-4,5-di-O-benzyl-2,6-dideoxy-2,6-imino-L-gulonate | 372494-20-7

• 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 N-benzyloxycarbonyl-4,5-di-O-benzyl-2,6-dideoxy-2,6-imino-L-gulonate
• CAS: 372494-20-7
• 化学式: C₃₅H₃₅NO₇
• 分子量: 581.665
• InChiKey: HXVVAKKHDYKBNB-UYEZAFAQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.28
• 重原子数：
  43.0
• 可旋转键数：
  11.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  94.53
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  benzyl N-benzyloxycarbonyl-4,5-di-O-benzyl-2,6-dideoxy-2,6-imino-L-gulonate 在 N-碘代丁二酰亚胺 、 4 Angstroem MS 、 三乙基硅基三氟甲磺酸酯 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 吡啶 、 乙醚 、 二氯甲烷 、 水 、 1,2-二氯乙烷 为溶剂， 反应 22.5h， 生成 benzyl 3-O-(2-acetamido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-N-benzyloxycarbonyl-4,5-di-O-benzyl-2,6-dideoxy-2,6-imino-L-gulonate
  参考文献：
  名称：

  Design and synthesis of a heparanase inhibitor with pseudodisaccharide structure

  摘要：

  Aza-analogue of the basic disaccharide unit of heparane sulfate was designed as a potent inhibitor against heparanase produced by solid tumors cell, and synthesized via a coupling reaction of phenyl 2-azide-1-thio-D-glucopyranoside derivatives with a partially protected 1-deoxynojirimycin derived from D-glucose. The azapseudodisaccharide inhibited tumor cell heparanase with IC50 value of 58-63 muM. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00642-1
• 作为产物：
  描述：

  benzyl 3-O-allyl-N-benzyloxycarbonyl-4,5-di-O-benzyl-2,6-dideoxy-2,6-imino-L-gulonate 在 palladium dichloride sodium acetate 、 溶剂黄146 作用下， 以 水 为溶剂， 反应 1.5h， 以74%的产率得到benzyl N-benzyloxycarbonyl-4,5-di-O-benzyl-2,6-dideoxy-2,6-imino-L-gulonate
  参考文献：
  名称：

  Design and synthesis of a heparanase inhibitor with pseudodisaccharide structure

  摘要：

  Aza-analogue of the basic disaccharide unit of heparane sulfate was designed as a potent inhibitor against heparanase produced by solid tumors cell, and synthesized via a coupling reaction of phenyl 2-azide-1-thio-D-glucopyranoside derivatives with a partially protected 1-deoxynojirimycin derived from D-glucose. The azapseudodisaccharide inhibited tumor cell heparanase with IC50 value of 58-63 muM. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00642-1