4-O-(2-azido-3,4-di-O-benzyl-2-deoxy-6-O-p-methoxybenzyl-α-D-glucopyranosyl)-N-benzyloxycarbonyl-2,3-di-O-benzyl-6-O-tert-butyldiphenylsilyl-1,5-dideoxy-1,5-imino-D-gulcitol | 161045-55-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-O-(2-azido-3,4-di-O-benzyl-2-deoxy-6-O-p-methoxybenzyl-α-D-glucopyranosyl)-N-benzyloxycarbonyl-2,3-di-O-benzyl-6-O-tert-butyldiphenylsilyl-1,5-dideoxy-1,5-imino-D-gulcitol
• 英文别名: benzyl (2R,3R,4R,5S)-3-[(2S,3R,4R,5S,6R)-3-azido-6-[(4-methoxyphenyl)methoxymethyl]-4,5-bis(phenylmethoxy)oxan-2-yl]oxy-2-[[tert-butyl(diphenyl)silyl]oxymethyl]-4,5-bis(phenylmethoxy)piperidine-1-carboxylate
• CAS: 161045-55-2
• 化学式: C₇₂H₇₈N₄O₁₁Si
• 分子量: 1203.52
• InChiKey: ANQUWFRFIRGZEO-CULIAMOKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.94
• 重原子数：
  88
• 可旋转键数：
  29
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  127
• 氢给体数：
  0
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  4-O-(2-azido-3,4-di-O-benzyl-2-deoxy-6-O-p-methoxybenzyl-α-D-glucopyranosyl)-N-benzyloxycarbonyl-2,3-di-O-benzyl-6-O-tert-butyldiphenylsilyl-1,5-dideoxy-1,5-imino-D-gulcitol 在 四丁基氟化铵 、 溶剂黄146 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 41.0h， 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-O-allyl-2-O-benzyl-N-benzyloxycarbonyl-1,5-dideoxy-1,5-imino-D-gulcitol 在 palladium dichloride 咪唑 、 N-碘代丁二酰亚胺 、 三氟甲磺酸 、 4 Angstroem MS 、 sodium acetate 、 四丁基碘化铵 、 sodium hydride 作用下， 以 乙醚 、 二氯甲烷 、 水 、 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.33h， 生成 4-O-(2-azido-3,4-di-O-benzyl-2-deoxy-6-O-p-methoxybenzyl-α-D-glucopyranosyl)-N-benzyloxycarbonyl-2,3-di-O-benzyl-6-O-tert-butyldiphenylsilyl-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

文献信息

• 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。
• 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.