13042-55-2

Usage

Class

Polyols and sugar alcohols

Derivative of

Xylitol (a five-carbon sugar alcohol)

Usage

Sugar substitute in food and pharmaceutical products

Potential Applications

a. Inhibitor of certain enzymes
b. Therapeutic agent for various diseases

Studied Properties

a. Anti-tumor
b. Anti-viral
c. Anti-fungal

Exploring Treatments

a. Diabetes
b. Metabolic disorders

Ongoing Research

Medical and industrial applications

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

Upstream product

• 130471-82-8 (3R,4r,5S)-1-benzylpiperidine-3,4,5-triol 
• 4711-03-9 5-azido-5-deoxy-1,2-O-isopropylidene-α-D-xylofuranose 
• 13042-52-9 5-Carbobenzoxyamino-5-desoxy-1,2-isopropyliden-D-xylofuranose 
• 4613-58-5 5-amino-5-deoxy-1,2-O-isopropylidene-a-D-xylofuranose 
• 131053-15-1 5-azido-3-O-benzyl-5-deoxy-1,2-O-isopropylidene-α-D-xylofuranose 
• 582-52-5 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 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 
• 13407-35-7 (2R,3R,4S,5S)-2,3,4,5-Tetrahydroxy-piperidine-1-carboxylic acid benzyl ester 
• 118495-40-2 (3R,5R)-1-Benzyl-3,4,5-tris-benzyloxy-piperidine 
• 7757-38-2 2,3,5,6-di-O-isopropylidene-D-mannofuranose 
• 530-26-7 D-Mannose 
• 54469-08-8 phenylmethyl 2,3:5,6-di-O-(1-methylethylidene)-α-D-mannofuranoside 
• 74912-02-0 1-O-benzyl-2,3-O-isopropylidene-α-D-manno-furanose 

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 academic research and scientific papers

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.

Chemo-enzymatic synthesis of polyhydroxyazepanes

Galactose oxidase (EC 1.1.3.9, GAO) is an extracellular copper-containing enzyme that utilizes molecular oxygen to convert the C6-primary hydroxyl moiety of D-galactopyranosides to hydrated aldehydes. Subsequent dehydratative coupling with hydroxylamines produces oximes (3a-f), which, when subjected to conditions of hydrogenolysis, give rise to polyhydroxyazepanes (11-17).

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.

Conversion of glycals into vicinal-1,2-diazides and 1,2-(or 2,1)-azidoacetates using hypervalent iodine reagents and Me3SiN3. Application in the synthesis of: N -glycopeptides, pseudo-trisaccharides and an iminosugar

Glycals were found to react with a reagent system comprising of phenyliodine bis(trifluoroacetate) (PIFA) and Me3SiN3 in the presence of TMSOTf as a catalyst to form the corresponding vicinal 1,2-diazides. On the other hand, they rea

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.

Double reductive amination and selective strecker reaction of a D-lyxaric aldehyde: Synthesis of diversely functionalized 3,4,5-trihydroxypiperidines

A D-mannose-derived aldehyde with the D-lyxo configuration is a versatile key intermediate to functionally and stereochemically diversified piperidines. It allowed the synthesis of natural 3,4,5-trihydroxypiperidines and new analogs through a double reductive amination strategy and the synthesis of novel 2-cyanotrihydroxypiperidines through a highly regio-and diastereoselective Strecker reaction.

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

SYNTHETIC ANALOGUES OF PHOSPHATIDYL-MYO-INOSITOL MANNOSIDES WITH AN INHIBITORY ACTIVITY OF THE INFLAMMATORY RESPONSE

The present invention relates to novel synthetic analogues of phosphatidyl-myo-inositol mannosides (hereinafter referred to as PIMs) of general formula (I): or a pharmaceutically acceptable salt thereof, to the method for preparing same and to the use thereof in the prevention or treatment of a disease associated with the overexpression of cytokines or of chemokines, in particular of TNF and/or of IL-12. The invention also relates to a pharmaceutical composition comprising at least one synthetic derivative of PIM.

A new route to diverse 1-azasugars from N-Boc-5-hydroxy-3-piperidene as a common building block

A new general method for the synthesis of a variety of 1-azasugars with a nitrogen atom at the anomeric position is described. The readily available chiral N-Boc-5-hydroxy-3-piperidene 3 is transformed to isofagomine (2), homoisofagomine (13), and 5′-deox