N-benzyloxycarbonyl-2,3-di-O-benzyl-6-O-tert-butyldiphenylsilyl-1,5-dideoxy-1,5-imino-D-gulcitol | 161045-53-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 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,4S,5S)-2-[[tert-butyl(diphenyl)silyl]oxymethyl]-3-hydroxy-4,5-bis(phenylmethoxy)piperidine-1-carboxylate
• CAS: 161045-53-0
• 化学式: C₄₄H₄₉NO₆Si
• 分子量: 715.962
• InChiKey: NUWUNAWKCDQTRD-SZRGUQLDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.12
• 重原子数：
  52
• 可旋转键数：
  15
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  77.5
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-benzyloxycarbonyl-2,3-di-O-benzyl-6-O-tert-butyldiphenylsilyl-1,5-dideoxy-1,5-imino-D-gulcitol 在 六甲基磷酰三胺 、 四丁基氟化铵 、 sodium methylate 、 溶剂黄146 作用下， 以 四氢呋喃 、 吡啶 、 甲醇 、 二氯甲烷 为溶剂， 反应 68.5h， 生成 2,3-di-O-benzyl-N,6-O-carbonyl-1,5-dideoxy-1,5-imino-D-galactitol
  参考文献：
  名称：

  Chemical Transformation of a 1-Deoxynojirimycin Derivative into 1-Deoxymannojirimycin and 1-Deoxygalactostatin

  摘要：

  Treatment of 2,3-di-O-benzyl-N-benzyloxycarbonyl-6-O-t-butyldiphenylsilyl-1-5-dideoxy-1,5-imino-D-glucitol (4) with sodium hydride resulted in an intramolecular cyclization concomitant with silyl migration, giving the carbamate derivative 5 in good yield. This was efficiently converted into 1-deoxymannojirimycin (2) via regioselective p-toluenesulfonylation followed by an inversion reaction at the C-2 position. On the other hand, the monochloromethylsulfonate 10 obtained from 4 underwent configurational change at the C-4 position by the action of sodium benzoate. The resulting benzoate 11 was deprotected to afford 1-deoxygalactostatin (3).

  DOI：

  10.1080/07328309808005772
• 作为产物：
  描述：

  4-O-allyl-N-benzyloxycarbonyl-2,3-di-O-benzyl-6-O-tert-butyldiphenylsilyl-1,5-dideoxy-1,5-imino-D-gulcitol 在 sodium acetate 、 溶剂黄146 、 palladium dichloride 作用下， 生成 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：

  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

• 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。
• Takahashi, Shunya; Kuzuhara, Hiroyoshi, Bioscience, Biotechnology and Biochemistry, 1995, vol. 59, # 4, p. 762 - 764
  作者：Takahashi, Shunya、Kuzuhara, Hiroyoshi

  DOI：——

  日期：——
• 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.
• Chemical Transformation of a 1-Deoxynojirimycin Derivative into 1-Deoxymannojirimycin and 1-Deoxygalactostatin
  作者：Shunya Takahashi、Hiroyoshi Kuzuhara

  DOI：10.1080/07328309808005772

  日期：1998.1

  Treatment of 2,3-di-O-benzyl-N-benzyloxycarbonyl-6-O-t-butyldiphenylsilyl-1-5-dideoxy-1,5-imino-D-glucitol (4) with sodium hydride resulted in an intramolecular cyclization concomitant with silyl migration, giving the carbamate derivative 5 in good yield. This was efficiently converted into 1-deoxymannojirimycin (2) via regioselective p-toluenesulfonylation followed by an inversion reaction at the C-2 position. On the other hand, the monochloromethylsulfonate 10 obtained from 4 underwent configurational change at the C-4 position by the action of sodium benzoate. The resulting benzoate 11 was deprotected to afford 1-deoxygalactostatin (3).