13042-55-2

Basic information

• Product Name: 1,5-DIDEOXY-1,5-IMINO-XYLITOL
• Synonyms: 1,5-DIDEOXY-1,5-IMINO-XYLITOL;Piperidine-3,4,5-triol
• CAS NO: 13042-55-2
• Molecular Formula: C₅H₁₁NO₃
• Molecular Weight: 133.15
• Product Categories: pharmacetical
• Mol File: 13042-55-2.mol
• Article Data: 16

Chemical Properties

• Boiling Point: 282.6°Cat760mmHg
• Flash Point: 161.3°C
• Appearance: /
• Density: 1.424g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.582
• CAS DataBase Reference: 1,5-DIDEOXY-1,5-IMINO-XYLITOL(CAS DataBase Reference)
• NIST Chemistry Reference: 1,5-DIDEOXY-1,5-IMINO-XYLITOL(13042-55-2)
• EPA Substance Registry System: 1,5-DIDEOXY-1,5-IMINO-XYLITOL(13042-55-2)

Safety Data

• Hazardous Substances Data: 13042-55-2(Hazardous Substances Data)

Usage

General Description

1,5-DIDEOXY-1,5-IMINO-XYLITOL, also known as dideoxyimino xylitol, is a synthetic compound that belongs to the class of polyols and sugar alcohols. It is a derivative of xylitol, a five-carbon sugar alcohol commonly used as a sugar substitute in food and pharmaceutical products. 1,5-DIDEOXY-1,5-IMINO-XYLITOL is known for its potential as an inhibitor of certain enzymes and as a potential therapeutic agent in the treatment of various diseases. It has been studied for its potential anti-tumor, anti-viral, and anti-fungal properties, and is also being explored as a potential treatment for diabetes and metabolic disorders. Further research is being conducted to explore the potential medical and industrial applications of this compound.

InChI:InChI=1/C5H11NO3/c7-3-1-6-2-4(8)5(3)9/h3-9H,1-2H2/t3-,4+,5+

Upstream product

• 4711-03-9 5-azido-5-deoxy-1,2-O-isopropylidene-α-D-xylofuranose 
• 30694-84-9 2,3-4,5-di-O-isopropylidene-D-xylonic acid methyl ester 
• 350255-13-9 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 908142-25-6 1-2 O-isopropylidene 3-O-benzyl α(D)gluco-pentoaldofuranose 
• 82805-13-8 5-bromo-5-deoxy-D-arabinono-1,4-lactone 
• 116661-76-8 1,5-anhydro-3,4-di-O-benzyl-2-deoxy-D-erythro-pent-1-enitol 
• 170554-25-3 (3aR,7R,7aS)-2,2-dimethylhexahydro[1,3]dioxolo[4,5-c]pyridin-7-ol 
• 102919-04-0 benzyl 2,3-O-isopropylidene-α-D-lyxo-pentodialdo-1,4-furanoside 
• 74912-02-0 1-O-benzyl-2,3-O-isopropylidene-α-D-manno-furanose 
• 54469-08-8 phenylmethyl 2,3:5,6-di-O-(1-methylethylidene)-α-D-mannofuranoside 
• 530-26-7 D-Mannose 
• 7757-38-2 2,3,5,6-di-O-isopropylidene-D-mannofuranose 
• 177567-99-6 1,2,3-tri-O-acetyl-5-azido-5-deoxy-D-arabinofuranose 
• 187144-36-1 (3S,4R,5R)-3,4,5-Trihydroxy-piperidin-2-one 

Downstream Products

• 1323207-86-8 benzyl (3S,4S,5R)-3,4-diacetoxy-5-(tri-O-acetyl-β-D-xylopyranosyloxy)piperidine-1-carboxylate 
• 1323207-91-5 benzyl (3S,4S,5R)-3,4-diacetoxy-5-[tri-O-acetyl-β-D-xylopyranosyl-(1->4)-di-O-acetyl-β-D-xylosyl-(1->4)-di-O-acetyl-β-D-xylosyloxy]piperidine-1-carboxylate 
• 448926-96-3 N-hexyl-1,5-dideoxy-1,5-iminoxylitol 

Relevant articles and documents

Synthesis of 1,5-dideoxy-1,5-imino-D-arabinitol (5-nor-L-fuco-1-deoxynojirimycin) and its application for the affinity purification and characterisation of α-L-fucosidase

The title, 1,5-dideoxy-1,5-imino-D-arabinitol (2), was synthesized in seven steps from D-arabinose with 5-azido-5-deoxy-D-arabinofuranose as key intermediate and 40percent overall yield.An affinity procedure employing the N-carboxypentyl derivative of 2 l

Deoxyiminoalditols from aldonolactones - V. Preparation of the four stereoisomers of 1,5-dideoxy-1,5-iminopentitols. Evaluation of these iminopentitols and three 1,5-dideoxy-1,5-iminoheptitols as glycosidase inhibitors

The four stereoisomeric 1,5-dideoxy-1,5-iminopentitols with D-arabino - (D-lyxo-) (3), ribo- (9), L-lyxo- (L-arabino-) (13) and xylo- (18) configurations were synthesized. The corresponding aldonolactones (1, 7 and 11) or aldonic acid ester (15b) having a leaving group at C-5 gave by reaction with aqueous ammonia, the 5-amino-5-deoxy-1,5-lactams, 2, 8, 12 and 17, respectively. Reduction of the lactam function using sodium borohydride/acetic or trifluoroacetic acid, or borane dimethyl sulfide complex yielded the iminopentitols. The compounds 3, 9, 13 and 18, together with the three 1,5-dideoxy-1,5-iminoheptitols 19, 20 and 21 were tested for inhibition of the glycosidase activities present in an extract from human liver. Compound 18 was a potent and 19 a moderately good inhibitor of β-glucosidase. Compound 3 together with 19, 20 and 21, all having D-arabino-configuration at the hydroxy-substituted carbon atoms, were good inhibitors of α-L-fucosidase.

Synthesis of new N-containing maltooligosaccharides, α-amylase inhibitors, and their biological activities

Fifteen new N-containing maltooligosaccharides were obtained using the chemoenzymatic method. Among these compounds, maltooligosaccharides having 6- amino-6-deoxy-D-sorbitol residue, (3R,4R,5R,6S)-hexahydro-3,4,5,6- tetrahydroxy-1H-azepine residue, and (3R,5R)-3,4,5-trihydroxypiperidine residue at the reducing end showed strong inhibitory activities for human pancreatic α-amylase (HPA) (EC 3.2.1.1) and human salivary amylase (HSA). The administration of (3R,4R,5R,6S)-hexahydro-3,5,6-trihydroxy-1H-azepine-4- yl O-α-D-glucopyranosyl-(1→4)-α-D-glucopyranoside (13, IC50=4.3x10-5M for HPA, IC50=8.2x10-5M for HSA) and (3R,5R)-3,5-dihydroxypiperidine-4- yl O-α-D-glucopyranosyl-(1→4)-α-D-glucopyranoside (18, IC50=3.4x10-5M for HPA, IC50=4.6 x 10-5 M for HSA) to ICR mice suppressed postprandial hyperglycemia.

Preparation of Z-α,β-unsaturated diazoketones from aldehydes. Application in the construction of substituted dihydropyridin-3-ones

The stereoselective preparation of α,β-unsaturated diazoketones with Z geometry is described from aldehydes and a new olefination reagent. When prepared from amino aldehydes, these diazoketones could be converted to substituted dihydropyridin-3-ones in just one step, after an intramolecular N-H insertion reaction. The straightforward synthesis of a natural trihydroxylated piperidine demonstrates the utility of these unsaturated diazoketones for the rapid construction of piperidines.

Glycosynthase-Mediated Assembly of Xylanase Substrates and Inhibitors

An exo-β-xylosidase mutant with glycosynthase activity was created to aid in the synthesis of xylanase substrates and inhibitors. Simple monosaccharides were easily elaborated into di-, tri- and tetrasaccharides by using this enzyme. Some products proved