69567-11-9

Basic information

• Product Name: Piperidine,3,4,5-tris(phenylmethoxy)-2-[(phenylmethoxy)methyl]-,(2R,3R,4R,5S)-
• Synonyms: Piperidine,3,4,5-tris(phenylmethoxy)-2-[(phenylmethoxy)methyl]-,(2R,3R,4R,5S)-;Deoxynojirimycin Tetrabenzyl Ether;Deoxynojirimycin Tetrabenzyl Ether Exclusive;3,4,5-tris(benzyloxy)-2-((benzyloxy)methyl)piperidine;3,4,5-tris(benzyloxy)-2-((benzyloxy)methyl)piperidine(WXC06522)
• CAS NO: 69567-11-9
• Molecular Formula: C₃₄H₃₇NO₄
• Molecular Weight: 523.66
• Product Categories: Sugars
• Mol File: 69567-11-9.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Piperidine,3,4,5-tris(phenylmethoxy)-2-[(phenylmethoxy)methyl]-,(2R,3R,4R,5S)-(CAS DataBase Reference)
• NIST Chemistry Reference: Piperidine,3,4,5-tris(phenylmethoxy)-2-[(phenylmethoxy)methyl]-,(2R,3R,4R,5S)-(69567-11-9)
• EPA Substance Registry System: Piperidine,3,4,5-tris(phenylmethoxy)-2-[(phenylmethoxy)methyl]-,(2R,3R,4R,5S)-(69567-11-9)

Safety Data

• Hazardous Substances Data: 69567-11-9(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
Piperidine,3,4,5-tris(phenylmethoxy)-2-[(phenylmethoxy)methyl]-,(2R,3R,4R,5S)is used as a building block in organic synthesis for the creation of other complex organic compounds. Its unique structure and functional groups make it a valuable intermediate in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, Piperidine,3,4,5-tris(phenylmethoxy)-2-[(phenylmethoxy)methyl]-,(2R,3R,4R,5S)is used as a potential candidate for drug development. Its specific stereochemistry and functional groups may confer pharmacological properties that can be harnessed for therapeutic applications, such as modulating biological targets or interacting with specific receptors.
Used in Pharmaceutical Industry:
Piperidine,3,4,5-tris(phenylmethoxy)-2-[(phenylmethoxy)methyl]-,(2R,3R,4R,5S)is used as a key intermediate in the production of pharmaceutical compounds. Its unique structure and stereochemistry may contribute to the development of new drugs with improved efficacy, selectivity, and safety profiles.
Used in Agrochemical Industry:
In the agrochemical industry, Piperidine,3,4,5-tris(phenylmethoxy)-2-[(phenylmethoxy)methyl]-,(2R,3R,4R,5S)is used as a precursor for the synthesis of agrochemicals, such as pesticides and herbicides. Its unique structure and functional groups may provide new opportunities for the development of more effective and environmentally friendly agrochemicals.
Further research and analysis are necessary to fully understand the properties and potential uses of Piperidine,3,4,5-tris(phenylmethoxy)-2-[(phenylmethoxy)methyl]-,(2R,3R,4R,5S)-, as well as to optimize its synthesis and application in various industries.

Upstream product

• 76670-94-5 2,3,4,6-tetra-O-benzyl-5-dehydro-5-oxo-D-gluconamide 
• 13096-62-3 (3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one 
• 100-46-9 benzylamine 
• 86496-30-2 (2S,3R,4R,5R)-2,3,4,6-tetrakis(benzyloxy)-5-hydroxyhexanal oxime 
• 4291-69-4 2,3,4,6-Tetra-O-benzyl-D-glucopyranose 
• 3879-79-6 methyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside 
• 100-39-0 benzyl bromide 
• 97-30-3 methyl-alpha-D-glucopyranoside 
• 139189-62-1 2,3,4,6-tetra-O-benzyl-L-idononitrile 
• 139189-57-4 2,3,4,6-tetra-O-benzyl-D-glucononitrile 
• 139189-63-2 2,3,4,6-tetra-O-benzyl-5-O-(4-toluenesulfonyl)-L-idononitrile 
• 139189-61-0 2,3,4,6-tetra-O-benzyl-D-xylo-hex-5-ulosononitrile 
• 139189-58-5 2,3,4,6-tetra-O-benzyl-5-bromo-5-deoxy-L-idononitrile 
• 72458-46-9 N-benzyl-1-deoxynojirimycin 

Downstream Products

• 219717-72-3 N--2,3,4,6-tetra-O-benzyl-1,5-dideoxy-1,5-imino-D-glucitol 
• 72599-27-0 N-butyldeoxynojirimycin 

Relevant articles and documents

Design, synthesis, and preliminary immunopotentiating activity of new analogues of nojirimycin

Three new classes of nojirimycin analogues viz. N-alkyl with C1-substituent (4-phenylbutyl), N-substituted 1-deoxynojirimycin and its congener δ-lactam, and a 4-phenylbutyl-β-C-glycoside were designed and synthesized for immunological studies. The resulti

Tuning the activity of iminosugars: novel N-alkylated deoxynojirimycin derivatives as strong BuChE inhibitors

We have designed unprecedented cholinesterase inhibitors based on 1-deoxynojirimycin as potential anti-Alzheimer’s agents. Compounds are comprised of three key structural motifs: the iminosugar, for interaction with cholinesterase catalytic anionic site (

Design, synthesis, and activity evaluation of novel N-benzyl deoxynojirimycin derivatives for use as α-glucosidase inhibitors

To obtain α-glucosidase inhibitors with high activity, 19 NB-DNJDs (N-benzyldeoxynojirimycin derivatives) were designed and synthesized. The results indicated that the 19 NBDNJDs displayed different inhibitory activities towards α-glucosidase in vitro. Compound 18a (1- (4-hydroxy-3-methoxybenzyl)-2-(hydroxymethyl) piperidine-3,4,5-triol) showed the highest activity, with an IC50 value of 0.207 ± 0.11 mM, followed by 18b (1-(3-bromo-4-hydroxy-5- methoxybenzyl)-2-(hydroxymethyl) piperidine-3,4,5-triol, IC50: 0.276 ± 0.13 mM). Both IC50 values of 18a and 18b were significantly lower than that of acarbose (IC50: 0.353 ± 0.09 mM). According to the structure-activity analysis, substitution of the benzyl and bromine groups on the benzene ring decreased the inhibition activity, while methoxy and hydroxyl group substitution increased the activity, especially with the hydroxyl group substitution. Molecular docking results showed that three hydrogen bonds were formed between compound 18a and amino acids in the active site of α- glucosidase. Additionally, an arene-arene interaction was also modelled between the phenyl ring of compound 18a and Arg 315. The three hydrogen bonds and the arene-arene interaction resulted in a low binding energy (-5.8 kcal/mol) and gave 18a a higher inhibition activity. Consequently, compound 18a is a promising candidate as a new α-glucosidase inhibitor for the treatment of type II diabetes.

Synthesis of 1-deoxynojirimycin: Exploration of optimised conditions for reductive amidation and separation of epimers

1-Deoxynojirimycin (DNJ), which has importance with respect to sugar processing enzymes, is a synthetic target for chemists. A key step in the synthesis of DNJ is the preparation of 2,3,4,6-tetra-O-benzyl-D-glucono-δ-lactam. By varying reaction parameters such as temperature, solvent and reducing reagent, improvements on previous methods are described. A novel approach for the synthesis of 2,3,4,6-tetra-O-benzyl-5-dehydro-5-deoxo-D-gluconamide has been developed by using PCC as an oxidising agent. Separation of epimers permitted DNJ to be obtained in 85% yield after reduction and hydrogenolysis steps.

A Fluorescence Polarization Activity-Based Protein Profiling Assay in the Discovery of Potent, Selective Inhibitors for Human Nonlysosomal Glucosylceramidase

Human nonlysosomal glucosylceramidase (GBA2) is one of several enzymes that controls levels of glycolipids and whose activity is linked to several human disease states. There is a major need to design or discover selective GBA2 inhibitors both as chemical tools and as potential therapeutic agents. Here, we describe the development of a fluorescence polarization activity-based protein profiling (FluoPol-ABPP) assay for the rapid identification, from a 350+ library of iminosugars, of GBA2 inhibitors. A focused library is generated based on leads from the FluoPol-ABPP screen and assessed on GBA2 selectivity offset against the other glucosylceramide metabolizing enzymes, glucosylceramide synthase (GCS), lysosomal glucosylceramidase (GBA), and the cytosolic retaining β-glucosidase, GBA3. Our work, yielding potent and selective GBA2 inhibitors, also provides a roadmap for the development of high-throughput assays for identifying retaining glycosidase inhibitors by FluoPol-ABPP on cell extracts containing recombinant, overexpressed glycosidase as the easily accessible enzyme source.

Concise synthesis of 1-epi-castanospermine

1-epi-Castanospermine (5) was synthesized from readily available 2,3,4,6-tetra-O-benzyl-1-deoxynojirimycin (11) in 9 steps and 21% overall yield, with selective debenzylation, Barbier reaction and reductive amination as the main reaction steps.

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.

A Click Ligation Based on SuFEx for the Metal-Free Synthesis of Sugar and Iminosugar Clusters

Although the preparation of anomeric glycosylsulfonyl fluoride was unsuccessful, a tetra-O-acetylated C-glucosylpropanesulfonyl fluoride was synthesized starting from the corresponding thioacetate via sulfonate formation as the key intermediate. This sulfonyl fluoride was a bench-stable product that reacted promptly with primary and secondary alkylamines at 80 °C to give the corresponding sulfonamides in good yield. On the other hand, the same fluoride was inert toward arylamines whereas its precursor, the sulfonyl chloride, showed good reactivity. Another limitation of the acetylated sugar sulfonyl fluoride was its lack of reactivity with a multivalent aminated calixarene, this being due to acetyl transfer from the carbohydrate moiety to the amino groups of the scaffold. Fortunately, the tetra-O-benzylated C-glucosylpropanesulfonyl fluoride, prepared by the same reaction sequence employed for the synthesis of the acetylated analogue, reacted with the tetra-aminopropyl-calix[4]arene to afford the corresponding sulfonamide-linked sugar cluster in high isolated yield. A similar approach to the synthesis of calixarene-based iminosugar clusters was unsuccessful because 1-deoxynojirimycin sulfonyl fluoride derivatives could not be generated. However, a tetra-propylsulfonyl fluoride calixarene, obtained from the free-OH calix[4]arene through a three-step reaction sequence, underwent clean coupling with both C-glucosylpropylamine and N-aminopentyl-1-deoxy-deoxynojirimycin derivatives to give the corresponding tetravalent sugar and iminosugar clusters. This metal-free click reaction may constitute a valuable tool in the arsenal of ligation tools for the synthesis of multivalent carbohydrate architectures.

One pot oxidative dehydration - oxidation of polyhydroxyhexanal oxime to polyhydroxy oxohexanenitrile: A versatile methodology for the facile access of azasugar alkaloids

A unique oxidative dehydration-oxidation of polyhydroxy-oxime (7) to the corresponding ketonitrile (8) in one pot is reported for the first time in carbohydrate literature. Key ketonitrile intermediate (8) upon palladium hydroxide mediated cascade reaction afforded 1-deoxynojirimycin (DNJ) 1b in moderate diastereoselectivity. The cascade reaction involves the conversion of nitrile to amine, heteroannulation, reduction of the imine and subsequent debenzylation to furnish the azasugars. This oxidative dehydration-oxidation and reductive heteroannulation methodology is successfully utilized for the total synthesis of 1-deoxynojirimycin (1b), miglitol (2) and miglustat (3).

Selenoureido-iminosugars: A new family of multitarget drugs

Herein we report the synthesis of N-alkylated deoxynojirimycin derivatives decorated with a selenoureido motif at the hydrocarbon tether as an example of unprecedented multitarget agents. Title compounds were designed as dual drugs for tackling simultaneously the Gaucher disease (by selective inhibition of β-glucosidase, Ki= 1.6–5.5 μM, with improved potency and selectivity compared to deoxynojirimycin) and its neurological complications (by inhibiting AChE, Kiup to 5.8 μM). Moreover, an excellent mimicry of the selenoenzyme glutathione peroxidase was also found for the catalytic scavenging of H2O2(Kcat/Kuncatup to 640) using PhSH as a cofactor, with improved activity compared to known positive controls, like (PhSe)2and ebselen; therefore, such compounds are also excellent scavengers of peroxides, an example of reactive oxygen species present at high concentrations in patients of Gaucher disease and neurological disorders.