phenyl 2-azido-3,4-di-O-benzyl-2-deoxy-6-O-p-methoxybenzyl-1-thio-D-glucopyranoside | 161045-54-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl 2-azido-3,4-di-O-benzyl-2-deoxy-6-O-p-methoxybenzyl-1-thio-D-glucopyranoside
• 英文别名: (2R,3S,4R,5R)-5-azido-2-[(4-methoxyphenyl)methoxymethyl]-3,4-bis(phenylmethoxy)-6-phenylsulfanyloxane
• CAS: 161045-54-1
• 化学式: C₃₄H₃₅N₃O₅S
• 分子量: 597.735
• InChiKey: LHFGLTZMFFIVHQ-WAPOLKSXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  43
• 可旋转键数：
  14
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  85.8
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  phenyl 2-azido-3,4-di-O-benzyl-2-deoxy-6-O-p-methoxybenzyl-1-thio-D-glucopyranoside 在 N-碘代丁二酰亚胺 、 三氟甲磺酸 、 4 Angstroem MS 、 四丁基氟化铵 、 溶剂黄146 、 三苯基膦 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 41.83h， 生成 4-O-(2-acetamido-3,4-di-O-benzyl-2-deoxy-6-O-p-methoxybenzyl-α-D-glucopyranosyl)-N-benzyloxycarbonyl-2,3-di-O-benzyl-1,5-dideoxy-1,5-imino-D-gulcitol
  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：

  4-甲氧基氯苄 、 在 四丁基碘化铵 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 phenyl 2-azido-3,4-di-O-benzyl-2-deoxy-6-O-p-methoxybenzyl-1-thio-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of a Potential Heparanase Inhibitor

  摘要：

  基于肝素硫酸盐中基本二糖单元设计了一种氮杂类似物，作为针对实体瘤细胞产生的肝素酶的潜在抑制剂，并通过苯基2-叠氮基-1-硫代-D-吡�糖苷衍生物与部分保护的1-脱氧野尻霉素（来自D-葡萄糖）的偶联反应合成，随后进行亚胺酸形成、O-硫酸化等操作。

  DOI：

  10.1246/cl.1994.2119

文献信息

• Design and synthesis of a heparanase inhibitor with pseudodisaccharide structure
  作者：Shunya Takahashi、Hiroyoshi Kuzuhara、Motowo Nakajima

  DOI：10.1016/s0040-4020(01)00642-1

  日期：2001.8

  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.
• Synthesis of a Potential Heparanase Inhibitor
  作者：Shunya Takahashi、Hiroyoshi Kuzuhara

  DOI：10.1246/cl.1994.2119

  日期：1994.11

  Aza-analog of the basic disaccharide unit in heparan sulfate was designed as a potential inhibitor against heparanase produced by solid tumor cells, and synthesized via a coupling reaction of a phenyl 2-azido-1-thio-d-glucopyranoside derivative with a partially protected 1-deoxynojirymycin derived from d-glucose, followed by manipulation such as imino acid formation, O-sulfation.

  基于肝素硫酸盐中基本二糖单元设计了一种氮杂类似物，作为针对实体瘤细胞产生的肝素酶的潜在抑制剂，并通过苯基2-叠氮基-1-硫代-D-吡�糖苷衍生物与部分保护的1-脱氧野尻霉素（来自D-葡萄糖）的偶联反应合成，随后进行亚胺酸形成、O-硫酸化等操作。