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
• Article Data: 24

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

General Description

Piperidine, 3,4,5-tris(phenylmethoxy)-2-[(phenylmethoxy)methyl]-(2R,3R,4R,5S) is a complex organic compound consisting of a piperidine ring with three phenylmethoxy groups attached at positions 3, 4, and 5, as well as a [(phenylmethoxy)methyl] group at position 2. The stereochemistry of the compound is indicated by the (2R,3R,4R,5S) designation. This chemical may have potential applications in organic synthesis or medicinal chemistry due to its unique structure and pharmacological properties. Additionally, it may be used as a building block or intermediate in the production of other compounds. Further research and analysis would be necessary to fully understand the properties and potential uses of this chemical.

Upstream product

• 139189-64-3 (5R,6R,7S,8S)-6,7,8-tris(benzyloxy)-5-<(benzyloxy)methyl>-5,6,7,8-tetrahydro-tetrazolo<1,5-a>pyridine 
• 77174-08-4 (3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)piperidin-2-one 
• 149302-60-3 N-benzyl-2,3,4,6-tetra-O-benzyl-1-deoxynojirimycin 
• 162119-08-6 [1S-(1α,2β,3α,4β,5α)]-2-(methoxyamino)-3,4,5-tris-(phenylmethoxy)-1-[(phenylmethoxy)methyl]cyclopentanol 
• 214041-43-7 (2R,3R,4S)-2,3,4,6-tetrakis(benzyloxy)-5-oxohexanal 
• 76670-94-5 2,3,4,6-tetra-O-benzyl-5-dehydro-5-oxo-D-gluconamide 
• 396098-62-7 5,N-didehydro-2,3,4,6-tetra-O-benzyl-deoxynojirimycin 
• 4291-69-4 2,3,4,6-Tetra-O-benzyl-D-glucopyranose 
• 78136-16-0 2,3,4,6-tetra-O-benzyl-D-glucitol 
• 396098-61-6 N-chloro-2,3,4,6-tetra-O-benzyl-deoxynojirimycin 
• 162119-07-5 (2S,3R,4R,5R)-2,3,4,6-Tetrakis-benzyloxy-5-hydroxy-hexanal O-methyl-oxime 
• 162019-08-1 2,3,4,6-tetrakis-O-(phenylmethyl)-D-xylo-hexos-5-ulose 1-(O-methyloxime) 
• 6564-72-3 2,3,4,6-tetra-O-benzyl-D-glucopyranose 
• 59531-24-7 2,3,4,6-tetra-O-benzyl-D-glucopyranoside 

Downstream Products

• 149302-61-4 N-<(p-fluorophenoxy)ethyl>-2,3,4,6-tetra-O-benzyl-1-deoxynojirimycin 
• 19130-96-2 1,5-dideoxy-1,5-imino-D-glucitol 
• 162398-66-5 N-(3-Oxadecyl)-2,3,4,6-tetra-O-benzyl-1-deoxynojirimycin 
• 162398-47-2 N-(7-Oxadecyl)-2,3,4,6-tetra-O-benzyl-1-deoxynojirimycin 
• 205649-36-1 N--2,3,4,6-tetra-O-benzyl-1,5-dideoxy-1,5-imino-D-glucitol 
• 219717-72-3 N--2,3,4,6-tetra-O-benzyl-1,5-dideoxy-1,5-imino-D-glucitol 
• 203130-20-5 N-<<1R-(1α,2β,3α,4β,5β)>-<1-(tert-butyldimethylsilyloxymethyl)-1-hydroxy-2,3,4-tris(tert-butyldimethylsilyloxy)cyclopent-5-yl>aminothiocarbonyl>-2,3,6-tetra-O-benzyl-1,5-dideoxy-1,5-imino-D-glucitol 
• 396098-61-6 N-chloro-2,3,4,6-tetra-O-benzyl-deoxynojirimycin 
• 929619-01-2 2,3,4,6-tetra-O-benzyl-N-pent-4'-enoyl-1-deoxynojirimycin 
• 857254-45-6 2,3,4,6-tetra-O-benzyl-N-[5-(adamantan-1-yl-methoxy)-pentyl]-1-deoxynojirimycin 
• 216758-20-2 AMP-DNM 
• 929619-03-4 2,3,4-tri-O-benzyl-N-pent-4'-enoyl-1-deoxynojirimycin 
• 929619-02-3 6-O-acetyl-2,3,4-tri-O-benzyl-N-pent-4'-enoyl-1-deoxynojirimycin 
• 929619-05-6 2,3,4-tri-O-benzyl-6-O-[1-(adamantan-1-yl-methoxy)-pentyl]-1-deoxynojirimycin 

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

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.