227932-82-3

Basic information

• Product Name: N-butyl 2,3,4,6-tetra-O-benzyl-1,5-dideoxy-1,5-imino-D-glucitol
• Synonyms: N-butyl 2,3,4,6-tetra-O-benzyl-1,5-dideoxy-1,5-imino-D-glucitol
• CAS NO: 227932-82-3
• Molecular Weight: 579.78
• Mol File: 227932-82-3.mol

Chemical Properties

• CAS DataBase Reference: N-butyl 2,3,4,6-tetra-O-benzyl-1,5-dideoxy-1,5-imino-D-glucitol(CAS DataBase Reference)
• NIST Chemistry Reference: N-butyl 2,3,4,6-tetra-O-benzyl-1,5-dideoxy-1,5-imino-D-glucitol(227932-82-3)
• EPA Substance Registry System: N-butyl 2,3,4,6-tetra-O-benzyl-1,5-dideoxy-1,5-imino-D-glucitol(227932-82-3)

Safety Data

• Hazardous Substances Data: 227932-82-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
N-butyl 2,3,4,6-tetra-O-benzyl-1,5-dideoxy-1,5-imino-D-glucitol is used as a reactant in the synthesis of deoxynojirimycin and its N-butyl (N-Bu) derivatives. These synthesized compounds have potential applications in the development of drugs targeting various diseases, including metabolic disorders and certain types of cancer.
Used in Chemical Research:
In the field of chemical research, N-butyl 2,3,4,6-tetra-O-benzyl-1,5-dideoxy-1,5-imino-D-glucitol serves as a valuable compound for studying the properties and reactivity of complex organic molecules. Its unique structure allows researchers to explore new synthetic pathways and develop innovative strategies for the creation of novel chemical entities.
Used in Drug Delivery Systems:
Similar to gallotannin, N-butyl 2,3,4,6-tetra-O-benzyl-1,5-dideoxy-1,5-imino-D-glucitol could potentially be employed in the development of drug delivery systems. These systems could be designed to improve the bioavailability, targeting, and therapeutic efficacy of various drugs, particularly those derived from the synthesis of deoxynojirimycin and its N-butyl derivatives.

Upstream product

• 18721-03-4 n-butylammonium methanoate 
• 214041-43-7 (2R,3R,4S)-2,3,4,6-tetrakis(benzyloxy)-5-oxohexanal 
• 97-30-3 methyl-alpha-D-glucopyranoside 
• 100-39-0 benzyl bromide 
• 1912-32-9 n-butyl methanesulfonate 
• 69567-11-9 2,3,4,6-tetra-O-benzyl-1,5-dideoxy-1,5-imino-D-glucitol 
• 76670-94-5 2,3,4,6-tetra-O-benzyl-5-dehydro-5-oxo-D-gluconamide 
• 3879-79-6 methyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside 
• 109-73-9 N-butylamine 
• 17791-38-7 1,2,3,4,5,6-Hexa-O-benzyl-D-sorbitol 
• 78136-16-0 2,3,4,6-tetra-O-benzyl-D-glucitol 
• 78136-16-0 (2S,3R,4R,5S)-2,3,4,6-tetrakis(benzyloxy)hexane-1,5-diol 
• 4291-69-4 2,3,4,6-Tetra-O-benzyl-D-glucopyranose 
• 1316108-89-0 (2R,3R,4R,5S)-1,3,4,5-tetrakis(benzyloxy)-6-(pivaloyloxy)hexan-2-yl benzoate 

Downstream Products

• 72599-27-0 N-butyldeoxynojirimycin 

Relevant articles and documents

Total synthesis of N-butyl-1-deoxynojirimycin

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.

SYNTHESIS OF AN AZASUGAR AND THE INTERMEDIATES THEREOF

Process for the preparation of intermediates useful in the synthesis of miglustat and their use in its manufacture.

SYNTHESIS OF A GLYCOSYLTRANSFERASE INHIBITOR

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.

IMINOSUGAR IN CRYSTALLINE FORM

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.

Facile and stereo-controlled synthesis of 2-deoxynojirimycin, Miglustat and Miglitol

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

Synthesis of 1-deoxynojirimycin and N-butyl-1-deoxynojirimycin

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.