N-Benzhydryl-1-deoxynojirimycin | 132198-14-2

• 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-Benzhydryl-1-deoxynojirimycin
• 英文别名: (2R,3R,4R,5S)-1-benzhydryl-2-(hydroxymethyl)piperidine-3,4,5-triol
• CAS: 132198-14-2
• 化学式: C₁₉H₂₃NO₄
• 分子量: 329.396
• InChiKey: KIEOHSDEGULDGN-UKBAYJJMSA-N

物化性质

• 沸点：
  554.0±50.0 °C(Predicted)
• 密度：
  1.321±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  84.2
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-Benzhydryl-1-deoxynojirimycin 在 palladium dihydroxide 氢气 作用下， 以90%的产率得到1-脱氧野尻霉素
  参考文献：
  名称：

  一步法从二羰基糖中制得吡咯烷和哌啶氨基糖。1-deoxynojirimycin的简捷合成

  摘要：

  二羰基糖是通过双重还原胺化反应（NaCNBH 3，MeOH）进行立体选择性合成羟基化哌啶和吡咯烷的便​​利底物。使用这种策略，由5-酮-D-果糖（2，可商购）和5-酮-D-葡萄糖（2，5-脱水亚氨基-D-葡萄糖醇（1）和1-脱氧野rim霉素（3））制备。4）。

  DOI：

  10.1016/s0040-4039(00)97169-7
• 作为产物：
  描述：

  1,2-O-异亚丙基-D-呋喃葡萄糖 在 Dowex 50W-X₈ 、 溴 、 二正丁基氧化锡 、 sodium cyanoborohydride 、 溶剂黄146 作用下， 以 甲醇 、 水 为溶剂， 反应 59.67h， 生成 N-Benzhydryl-1-deoxynojirimycin
  参考文献：
  名称：

  Expeditious Synthesis of Aza sugars by the Double Reductive Amination of Dicarbonyl Sugars

  摘要：

  Polyhydroxylated pyrrolidines and piperidines were prepared by the double reductive amination of dicarbonyl, sugars with primary amines and NaCNBH3 in MeOH. Stereocontrol in these reactions depended on the nature of the amine and dicarbonyl sugar. For example, 5-keto-D-fructose (7) gave three pyrrolidine stereoisomers, with the N-alkylated 2,5-anhydro-2,5-imino-D-glucitol predominating. Under similar reaction conditions with benzhydrylamine, 5-keto-D-glucose (20) afforded a 96:4 mixture of piperidines favoring D-gluco 25A, whereas 5-keto-D-mannose (6) produced a 67:33 mixture enriched in D-manno isomer 40. This method allowed for the direct and relatively short synthesis of 1-deoxynojirimycin (DNJ, 1) and 1-deoxymannojirimycin (DMJ, 5) and N-alkylated derivatives thereof. Similar reactions with O-protected 5-keto-D-glucose derivatives 21 and 22 were less stereoselective and lower yielding.

  DOI：

  10.1021/jo00090a040

文献信息

• Synthesis and hybridization properties of oligonucleotides containing 6-membered azasugar nucleotides
  作者：Kyeong-Eun Jung、Kichul Kim、Mirim Yang、Kwangjun Lee、Hong Lim

  DOI：10.1016/s0960-894x(99)00619-8

  日期：1999.12

  modified nucleoside was synthesized with adenine and a 6-membered azasugar, and it was converted to the phosphoramidite which was used for the incorporation into oligonucleotides. The hybridization properties of the modified oligonucleotides with DNA and RNA were studied.

  用腺嘌呤和6-元氮杂糖合成修饰的核苷，并将其转化为亚磷酰胺，其用于掺入寡核苷酸中。研究了修饰寡核苷酸与DNA和RNA的杂交特性。
• Process for producing polyhydroxylated piperidines and pyrrolidines and
  申请人：McNeilab, Inc.

  公开号：US05290948A1

  公开（公告）日：1994-03-01

  A process for converting 1,4- and 1,5-dicarbonyl sugars to pyrrolidine and piperidine amino sugars. Novel compounds resulting from this process are also described.

  一种将1,4-和1,5-二羰基糖转化为吡咯烷和哌嗪氨基糖的过程。本发明还描述了由此过程产生的新化合物。
• Isotope edited NMR studies of glycosidases: design and synthesis of a novel glycosidase inhibitor
  作者：Jennifer V. Hines、Heesun Chang、Melinda S. Gerdeman、Dana E. Warn

  DOI：10.1016/s0960-894x(99)00175-4

  日期：1999.5

  N-C-13-methyl-deoxynojirimycin was synthesized and used in isotope-edited NMR studies to probe the binding site of an a-glucosidase. Results from this analysis led to the design and preparation of a novel alpha-glucosidase inhibitor, N-glycyl deoxynojirimycin. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Expeditious Synthesis of Aza sugars by the Double Reductive Amination of Dicarbonyl Sugars
  作者：Ellen W. Baxter、Allen B. Reitz

  DOI：10.1021/jo00090a040

  日期：1994.6

  Polyhydroxylated pyrrolidines and piperidines were prepared by the double reductive amination of dicarbonyl, sugars with primary amines and NaCNBH3 in MeOH. Stereocontrol in these reactions depended on the nature of the amine and dicarbonyl sugar. For example, 5-keto-D-fructose (7) gave three pyrrolidine stereoisomers, with the N-alkylated 2,5-anhydro-2,5-imino-D-glucitol predominating. Under similar reaction conditions with benzhydrylamine, 5-keto-D-glucose (20) afforded a 96:4 mixture of piperidines favoring D-gluco 25A, whereas 5-keto-D-mannose (6) produced a 67:33 mixture enriched in D-manno isomer 40. This method allowed for the direct and relatively short synthesis of 1-deoxynojirimycin (DNJ, 1) and 1-deoxymannojirimycin (DMJ, 5) and N-alkylated derivatives thereof. Similar reactions with O-protected 5-keto-D-glucose derivatives 21 and 22 were less stereoselective and lower yielding.
• Pyrrolidine and piperidine aminosugars from dicarbonyl sugars in one step. Concise synthesis of 1-deoxynojirimycin
  作者：Allen B. Reitz、Ellen W. Baxter

  DOI：10.1016/s0040-4039(00)97169-7

  日期：1990.1

  Dicarbonyl sugars are convenient substrates for the stereoselective synthesis of hydroxylated piperidines and pyrrolidines, via a double reductive amination reaction (NaCNBH3, MeOH). Using this strategy, 2,5-anhydro-imino-D-glucitol (1) and 1-deoxynojirimycin (3) were prepared from 5-keto-D-fructose (2, commercially available) and 5-keto-D-glucose (4), respectively.

  二羰基糖是通过双重还原胺化反应（NaCNBH 3，MeOH）进行立体选择性合成羟基化哌啶和吡咯烷的便​​利底物。使用这种策略，由5-酮-D-果糖（2，可商购）和5-酮-D-葡萄糖（2，5-脱水亚氨基-D-葡萄糖醇（1）和1-脱氧野rim霉素（3））制备。4）。