N-benzyloxycarbonyl-1,5-dideoxy-1,5-imino-D-glucitol | 130539-12-7

• 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-1,5-dideoxy-1,5-imino-D-glucitol
• 英文别名: benzyl (2R,3R,4R,5S)-3,4,5-trihydroxy-2-(hydroxymethyl)piperidine-1-carboxylate
• CAS: 130539-12-7
• 化学式: C₁₄H₁₉NO₆
• 分子量: 297.308
• InChiKey: OIBMNXFWGHCZMZ-YVECIDJPSA-N

物化性质

• 沸点：
  494.3±45.0 °C(Predicted)
• 密度：
  1.447±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  111
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-benzyloxycarbonyl-1,5-dideoxy-1,5-imino-D-glucitol 在 2,6-二甲基吡啶 、 palladium on activated charcoal 、 10 wt% Pd(OH)2 on carbon 、 氢气 作用下， 以 氯仿 、 乙酸乙酯 为溶剂， 反应 5.0h， 生成 [(2R,3R,4R,5S)-3,5-bis[[tert-butyl(dimethyl)silyl]oxy]-2-[[tert-butyl(dimethyl)silyl]oxymethyl]piperidin-4-yl]oxy-tert-butyl-dimethylsilane
  参考文献：
  名称：

  双靶向的多羟基生物碱类化合物及其制备方法和用途

  摘要：

  本发明提供了一种双靶向的多羟基生物碱类化合物及其制备方法和用途，涉及医药领域。本发明提供的双靶向的多羟基生物碱类化合物将1‑脱氧野尻霉素与噻唑烷二酮进行拼合，合成了新型的具有治疗糖尿病等作用的1‑脱氧野尻霉素衍生物，合成方法简便，产物纯度高。所述衍生物具有优异的α‑葡萄糖苷酶抑制活性，可以与PPARγ直接结合，从而改善胰岛素抵抗，提升降血糖效果。

  公开号：

  CN116621830A
• 作为产物：
  描述：

  1-脱氧野尻霉素 、 氯甲酸苄酯 在 sodium carbonate 作用下， 以 水 为溶剂， 以60%的产率得到N-benzyloxycarbonyl-1,5-dideoxy-1,5-imino-D-glucitol
  参考文献：
  名称：

  1,5-二脱氧-1,5-（烷基）亚氨基-2-C-甲基-d-葡萄糖醇的合成

  摘要：

  从脱氧野oji霉素开始，完成了标题化合物3和4的区域和立体选择性合成。讨论了影响格利雅（Grignard）加成关键羰基中间体的立体化学结果的因素。

  DOI：

  10.1016/0040-4039(96)00021-4

文献信息

• 2- and 3-sulfur derivatives of 1,5-iminosugars
  申请人：G.D. Searle & Co.

  公开号：US05342951A1

  公开（公告）日：1994-08-30

  Novel derivatives of 1-deoxynojirimycin are disclosed which have thio or sulfinyl substituents at C-2 or C-3. These compounds are useful inhibitors of lentiviruses such as visna virus and human immunodeficiency virus. Methods of chemical synthesis of these derivatives and intermediates therefor are also disclosed.

  揭示了1-去氧诺吉霉素的新衍生物，其在C-2或C-3处具有硫或亚砜取代基。这些化合物是猪萎缩病毒和人类免疫缺陷病毒等 lentivirus 的有用抑制剂。还公开了这些衍生物的化学合成方法和中间体。
• DEOXYNOJIRIMYCIN DERIVATIVES AND METHODS OF THEIR USING
  申请人：EMERGENT VIROLOGY LLC

  公开号：US20160221993A1

  公开（公告）日：2016-08-04

  The present application provide novel iminosugars and their use in treatment of viral infections, such as Dengue infection and Influenza A infection. The present inventors discovered certain deoxynojirimycin derivatives may be effective against one or more viruses, which may be, for example, a Dengue virus and/or a virus belonging to the Orthomyxoviridae family, such as an Influenza A virus. In particular, such deoxynojirimycin derivatives may be useful for treating a disease or condition caused by or associated with one or more viruses. In certain embodiments, the deoxynojirimycin derivatives may increase a survival rate or probability for a subject infected with one or more viruses, which may be, for example, a Dengue virus and/or a virus belonging to the Orthomyxoviridae family, such as an Influenza A virus.

  该申请提供了新型亚胺糖及其在治疗病毒感染方面的用途，例如登革热感染和甲型流感感染。本发明者发现某些脱氧诺吉霉素衍生物可能对一种或多种病毒有效，例如登革病毒和/或属于流感病毒科的病毒，如甲型流感病毒。特别是，这些脱氧诺吉霉素衍生物可能有助于治疗由一种或多种病毒引起或相关的疾病或症状。在某些实施方式中，这些脱氧诺吉霉素衍生物可能提高受感染的个体的存活率或概率，例如登革病毒和/或属于流感病毒科的病毒，如甲型流感病毒。
• Selective Protection/Deprotection in 1-Deoxynojirimycin Scaffold: Regioselective Mono-Benzoylation and Alkylation using TBAB-NaOH Catalytic System
  作者：Mehwish Iftikhar、Zhijie Fang

  DOI：10.17344/acsi.2018.4255

  日期：——

  carried out. Substrate N -benzyloxycarbonyl-1,5-dideoxy-1,5-imino-4,6- O -isopropylidene-D-glucitol was subjected to alkylation at positions 2- and 3- to obtain di-substituted products and N -Cbz group was selectively removed by using NaOH in EtOH/H 2 O. Regioselective benzoylation and alkylation of N -benzyloxycarbonyl-1,5-dideoxy-1,5-imino-4,6- O -isopropylidene-D-glucitol were conducted under the action

  保护基在碳水化合物化学中起重要作用，并极大地影响底物的反应性。对1-脱氧野oji霉素中各种保护基的取代进行了研究。使底物N-苄氧基羰基-1,5-二脱氧-1,5-亚氨基-4,6-O-异亚丙基-D-葡萄糖醇在位置2-和3-处烷基化以获得二取代的产物和N-Cbz基团通过在EtOH / H 2 O中使用NaOH选择性除去。N-苄氧基羰基-1,5-二脱氧-1,5-亚氨基-4,6-O-异亚丙基-D-葡萄糖醇的区域选择性苯甲酰化和烷基化的TBAB-NaOH催化体系。发现所有保护的和单保护的类似物同时形成，并且其结构通过光谱学方法证实。
• 1,5-dideoxy-1,5-imino-D-glucitol derivatives
  申请人：G. D. Searle & Co.

  公开号：US05221746A1

  公开（公告）日：1993-06-22

  O-acylated derivatives of 1,5-dideoxy-1,5-imino-D-glucitol are disclosed that contain an N-alkyl or N-aroyl radical in which from one to four of the free hydroxyl groups are O-acylated with carboxylic alkanoyl radicals selected from the group consisting of .omega.,.omega.,.omega.-trifluoro alkanoyl having from three to eight carbon atoms, carboxylic cycloalkanoyl groups having from four to eight carbon atoms and carboxylic acyclic alkanoyl groups having from two to ten carbon atoms, wherein the N-aroyl radical is selected from the group consisting of p-decylbenzoyl, 3-(p-chlorophenoxy)propanoyl, 2-(acetyloxy)benzoyl, [1,1'-biphenyl]-4-ylcarbonyl, 2-thiopheneacetyl, trans-3-furanacryloyl 3-methoxyphenylacetyl and 3-(trifluoromethyl)benzoyl, and wherein the N-alkyl contains from one to fourteen carbon atoms, provided that when N-alkyl contains from one to five carbon atoms the O-acylated groups are .omega.,.omega.,.omega.-trifluoro alkanoyl or carboxylic cycloalkanoyl.

  披露了1,5-二去氧-1,5-亚胺-D-葡萄糖醇的O-酰化衍生物，其中含有一个到四个自由羟基被选自以下羧基烷酰基的羧基烷酰基的N-烷基或N-芳酰基，.omega.，.omega.，.omega.-三氟烷酰基，碳原子数为三至八个，具有四至八个碳原子的羧基环烷酰基和具有两至十个碳原子的羧基无环烷酰基，其中N-芳酰基选自以下羧基苯基，3-(对氯苯氧基)丙酰基，2-(乙酰氧基)苯甲酰基，[1,1'-联苯]-4-基甲酰基，2-噻吩乙酰基，反式-3-呋喃丙烯基3-甲氧基苯乙酰基和3-(三氟甲基)苯甲酰基，其中N-烷基含有一个到十四个碳原子，前提是当N-烷基含有一个到五个碳原子时，O-酰化基团为.omega.，.omega.，.omega.-三氟烷酰基或羧基环烷酰基。
• Antiviral compounds
  申请人：G. D. Searle & Co.

  公开号：US05310745A1

  公开（公告）日：1994-05-10

  A method of inhibiting lentivirus is disclosed which comprises mammalian host susceptible to said lentivirus with a virally inhibitory effective amount of an O-acylated derivative of 1,5-dideoxy-1,5-imino-D-glucitol and their N-alkyl, N-acyl and N-aroyl derivatives in which from one to four of the free hydroxyl groups are O-acylated with carboxylic alkanoyl radicals selected from the group consisting of .omega.,.omega.,.omega.-trifluoroalkanoyl having from three to eight carbon atoms, carboxylic cycloalkanoyl groups having from four to eight carbon atoms and carboxylic acyclic alkanoyl groups having from two to ten carbon atoms, wherein the N-aroyl groups contain from 7 to 14 carbon atoms, the N-acyl groups contain from 4 to 8 carbon atoms and the N-alkyl groups contain from 1 to 14 carbon atoms.

  本发明揭示了一种抑制慢病毒的方法，包括将哺乳动物宿主暴露于所述慢病毒的有效抑制量的1,5-二去氧-1,5-亚胺-D-葡萄糖醇的O-酰化衍生物及其N-烷基，N-酰基和N-芳酰衍生物中，其中从一个到四个自由羟基被选自由三至八个碳原子的羧基烷酰基的.omega.，.omega.，.omega.-三氟烷酰基，含有四至八个碳原子的环烷基羧基和含有两至十个碳原子的无环烷基羧基，其中N-芳酰基含有七至十四个碳原子，N-酰基含有四至八个碳原子，N-烷基含有一至十四个碳原子。