- Total synthesis of N-butyl-1-deoxynojirimycin
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N-Butyl-1-deoxynojirimycin (NB-DNJ) derived from imino sugar deoxynojirimycin (DNJ) has been approved for the treatment of Gaucher’s disease. Herein, a facile and efficient synthetic procedure for NB-DNJ has been described. Comparing to the methods reported previously,methanesulfonyl group was used as a leaving group for easy displacement upon attack by the imine in the sugar ring, leading to a high yield during the introduction of the n-butyl group. Thismethod can serve as an excellent protocol for the synthesis of DNJ derivatives with a variety of N-alkyl substituents and for large-scale production.
- Wang, Jiajia,Zhao, Yunyan,Zhao, Wei,Wang, Peng,Li, Jing
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p. 445 - 454
(2017/08/23)
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- SYNTHESIS OF AN AZASUGAR AND THE INTERMEDIATES THEREOF
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Process for the preparation of intermediates useful in the synthesis of miglustat and their use in its manufacture.
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Paragraph 0051; 0052; 0053; 0054
(2016/12/07)
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- IMINOSUGAR IN CRYSTALLINE FORM
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Iminosugar, which possesses known activity as a glycosyltransferase inhibitor, and is used, for example, in the treatment of Gaucher's disease, in crystalline form, a process for its preparation and a pharmaceutical composition thereof.
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- SYNTHESIS OF A GLYCOSYLTRANSFERASE INHIBITOR
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Process for the preparation of animinosugar, and the intermediates thereof, having known activity as a glycosyltransferase inhibitor and used, for example, in the treatment of Gaucher's disease.
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Paragraph 0053; 0054
(2014/09/03)
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- Facile and stereo-controlled synthesis of 2-deoxynojirimycin, Miglustat and Miglitol
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A novel and facile synthesis of a series of the biologically significant iminosugar derivatives including 2-deoxynojirimycin, Miglustat and Miglitol is reported. The synthesis features a strategic double inversion mechanism for securing the desired stereochemistry at C5 position of such glucose-type carbohydrate mimetics, representing a practical and remarkable improvement on the previously reported method that suffers from the loss of the stereo-control during the reaction process. Crown Copyright
- Zhang, Zhen-Xing,Wu, Baolin,Wang, Bin,Li, Tie-Hai,Zhang, Peng-Fei,Guo, Li-Na,Wang, Wen-Jun,Zhao, Wei,Wang, Peng George
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p. 3802 - 3804
(2011/08/09)
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- Synthesis of 1-deoxynojirimycin and N-butyl-1-deoxynojirimycin
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1-Deoxynojirimycin (1) is a natural alkaloid with several biological activities; the analog N-butyl-1-deoxynojirimycin (4), for example has shown potent anti HIV-1 and HIV-2 activity without cytotoxicity. As part of a program to synthesize compounds with biological activity against retroviruses, we developed an efficient route for the preparation of 1 and 4 employing as raw material glucose and others inexpensive reagents.
- Matos, Carlos R. R.,Lopes, Rosangela S. C.,Lopes, Claudio C.
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p. 571 - 573
(2007/10/03)
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