10034-19-2

Basic information

• Product Name: 1,3,4,6-Tetra-O-acetyl-2-amino-2-deoxy-a-D-glucopyranose Hydrochloride
• Synonyms: 1,3,4,6-Tetra-O-acetyl-2-amino-2-deoxy-a-D-glucopyranose Hydrochloride;2-AMino-2-deoxy-α-D-glucopyranose 1,3,4,6-Tetraacetate Hydrochloride;2-Amino-1,3,4,6-tetra-O-acetyl-2-deoxy-alpha-D-glucopyranose hydrochloride
• CAS NO: 10034-19-2
• Molecular Formula: C₁₄H₂₂NO₉*Cl
• Molecular Weight: 383.77878
• Product Categories: Amines;Carbohydrates & Derivatives;Inhibitors
• Mol File: 10034-19-2.mol
• Article Data: 50

Chemical Properties

• Melting Point: 160-186 °C (decomp)
• Appearance: /
• Storage Temp.: -20°C Freezer
• Solubility: DMSO (Slightly), Methanol (Slightly), Water (Slightly)
• CAS DataBase Reference: 1,3,4,6-Tetra-O-acetyl-2-amino-2-deoxy-a-D-glucopyranose Hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3,4,6-Tetra-O-acetyl-2-amino-2-deoxy-a-D-glucopyranose Hydrochloride(10034-19-2)
• EPA Substance Registry System: 1,3,4,6-Tetra-O-acetyl-2-amino-2-deoxy-a-D-glucopyranose Hydrochloride(10034-19-2)

Safety Data

• Hazardous Substances Data: 10034-19-2(Hazardous Substances Data)

Usage

Chemical Properties

White Solid

Uses

Different sources of media describe the Uses of 10034-19-2 differently. You can refer to the following data:
1. A potential metabolic inhibitor of cellular-membrane glycoconjugates.
2. A potential metabolic inhibitor of cellular-membrane glycoconjugates

InChI:InChI=1/C14H21NO9.ClH/c1-6(16)20-5-10-12(21-7(2)17)13(22-8(3)18)11(15)14(24-10)23-9(4)19;/h10-14H,5,15H2,1-4H3;1H/t10?,11-,12+,13+,14-;/m0./s1

Upstream product

• 7597-81-1 1,3,4,6-tetra-O-acetyl-2-deoxy-2-(4-methoxybenzylidene)amino-β-D-glucopyranose 
• 7647-01-0 hydrogenchloride 
• 75-52-5 nitromethane 
• 3068-34-6 Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-chloro-tetrahydro-pyran-4-yl ester 
• 178158-22-0 tert-butyl ((2S,3R,4R,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-3-yl)carbamate 
• 14131-62-5 D-glucosamine hydrochloride 
• 10378-06-0 2-methyl-(3,4,6-tri-O-acetyl-1,2-dideoxy-α-D-glucopyranoso)[1,2-d]-2-oxazoline 
• 95900-18-8 Acetic acid (2R,3R,4R,5S,6R)-2,5-diacetoxy-6-acetoxymethyl-3-(2-acetyl-3-oxo-but-1-enylamino)-tetrahydro-pyran-4-yl ester 
• 1078691-95-8 (+)-D-glucosamine hydrochloride 
• 108-24-7 acetic anhydride 
• 130005-73-1 3,4,6-tri-O-acetyl-2-deoxy-2-p-methoxybenzylideneamino-β-D-glucopyranose 
• 90176-39-9 2-benzylideneamino-2-deoxy-β-D-glucopyranose 
• 14131-63-6 D-glucosamine hydrochloride 
• 75-36-5 acetyl chloride 

Downstream Products

• 141280-19-5 2--L-phenylalanylamido-2-deoxy-1,3,4,6-tetra-O-acetyl-β-D-glucose 
• 141280-14-0 2-(N-acetyl)-L-phenylalanylamido-2-deoxy-1,3,4,6-tetra-O-acetyl-β-D-glucose 
• 175229-70-6 1-acetoxy-3,4,6-tri-O-acetyl-2-deoxy-2-(4,5-dichlorophthalimido)-β-D-glucopyranoside 
• 52162-39-7 2-(benzylidene)amino-2-deoxy-1,3,4,6-tetra-O-acetyl-β-D-glucopyranose 
• 126946-45-0 (2S,3R,4R,5S,6R)-6-(acetoxymethyl)-3-(benzylamino)tetrahydro-2H-pyran-2,4,5-triyl triacetate 
• 870529-09-2 prop-2-enyl 2-{[(benzyloxy)carbonyl]amino}-2-deoxy-β-D-glucopyranosiduronic acid 
• 870529-38-7 [((2S,3S,4R,5R,6R)-5-Amino-3,4-dihydroxy-6-phenethyloxy-tetrahydro-pyran-2-carbonyl)-amino]-acetic acid methyl ester 
• 870529-08-1 3-methylbutyl 2-{[(benzyloxy)carbonyl]amino}-2-deoxy-β-D-glucopyranosiduronic acid 
• 874816-52-1 ((2R,3R,4R,5S,6R)-2-Hexyloxy-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl)-carbamic acid benzyl ester 
• 870529-11-6 hexyl 2-{[(benzyloxy)carbonyl]amino}-2-deoxy-β-D-glucopyranosiduronic acid 
• 870529-41-2 {[(2S,3S,4R,5R,6R)-5-Amino-3,4-dihydroxy-6-((1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyloxy)-tetrahydro-pyran-2-carbonyl]-amino}-acetic acid methyl ester 
• 870529-42-3 {[(2S,3S,4R,5R,6S)-5-Amino-3,4-dihydroxy-6-((1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyloxy)-tetrahydro-pyran-2-carbonyl]-amino}-acetic acid methyl ester 
• 870529-10-5 2-phenylethyl 2-{[(benzyloxy)carbonyl]amino}-2-deoxy-β-D-glucopyranosiduronic acid 
• 870529-02-5 prop-2-enyl 3,4,6-tri-O-acetyl-2-{[(benzyloxy)carbonyl]amino}-2-deoxy-β-D-glucopyranoside 

Relevant articles and documents

Synthesis and induction of apoptosis in B cell chronic leukemia by diosgenyl 2-amino-2-deoxy-β-D-glucopyranoside hydrochloride and its derivatives

2-Acetamido-2-deoxy-D-glucose hydrochloride (D-glucosamine hydrochloride) has been used for the preparation of 1,3,4,6-tetra-O-acetyl-2-deoxy-2-trifluoroacetamido-β- (4) and 2-tetrachlorophthalimido-α,β-D-glucopyranose (6), which have been transformed into the appropriate bromides and the chloride. Both bromo and chloro sugars were used as a glycosyl donors for the glycosylation of diosgenin [(25R)-spirost-5-en-3β-ol]. These condensations were conducted under mild conditions, using silver triflate as a promoter, and gave diosgenyl glycosides 9 and 12. Each of them was converted into diosgenyl 2-amino-2-deoxy-β-D-glucopyranoside hydrochloride (11) and N-acylamido derivatives. The structures of all new glycosides were established by 1H and 13C NMR spectroscopy. These diosgenyl glycosides are the first saponins containing the D-glucosamine residue that have been synthesized. These compounds show promising antitumor activities. The synthetic saponins increase the number of apoptotic B cells, in combination with cladribine (2-CdA), that are isolated from chronic lymphotic leukemia (B-CLL) patients.

Synthesis and biological activity of nitro heterocycles analogous to megazol, a trypanocidal lead

As part of our efforts to develop new compounds aimed at the therapy of parasitic infections, we synthesized and assayed analogues of a lead compound megazol, 5-(1-methyl-5-nitro-1H-2-imidazolyl)-1,3,4-thiadiazol-2-amine, CAS no. 19622-55-0), in vitro. We first developed a new route for the synthesis of megazol. Subsequently several structural changes were introduced, including substitutions on the two rings of the basic nucleus, replacement of the thiadiazole by an oxadiazole, replacement of the nitroimidazole part by a nitrofurane or a nitrothiophene, and substitutions on the exocyclic nitrogen atom for evaluation of an improved import by the glucose or the purine transporters. Assays of the series of compounds on the protozoan parasites Trypanosoma brucei, Trypanosoma cruzi, and Leishmania donovani, as either extracellular cells or infected macrophages, indicated that megazol was more active than the derivatives. Megazol was then evaluated on primates infected with Trypanosoma brucei gambiense, including late-stage central nervous system infections in combination with suramin. Full recovery was observed in five monkeys in the study with no relapse of parasitemia within a 2 year follow-up. Because there is a lack of efficacious treatments for sleeping sickness in Africa and Chagas disease in South America, megazol is proposed as a potential alternative. The mutagenicity of this compound is at present being reevaluated, and metabolism is also under investigation prior to possible further developments.

Synthesis of an Fmoc-threonine bearing core-2 glycan: A building block for PSGL-1 via Fmoc-assisted solid-phase peptide synthesis

Selectins (L, E, and P) are vascular endothelial molecules that play an important role in the recruitment of leukocytes to inflamed tissue. In this regard, P-Selectin glycoprotein-1 (PSGL-1) has been identified as a ligand for P-Selectin. PSGL-1 binds to

Total Synthesis of a Densely Functionalized Plesiomonas shigelloides Serotype 51 Aminoglycoside Trisaccharide Antigen

Plesiomonas shigelloides, a pathogen responsible for frequent outbreaks of severe travelers' diarrhea, causes grave extraintestinal infections. Sepsis and meningitis due to P. shigelloides are associated with a high mortality rate as antibiotic resistance increases and vaccines are not available. Carbohydrate antigens expressed by pathogens are often structurally unique and are targets for developing vaccines and diagnostics. Here, we report a total synthesis of the highly functionalized trisaccharide repeating unit 2 from P. shigelloides serotype 51 from three monosaccharides. A judicious choice of building blocks and reaction conditions allowed for the four amino groups adorning the sugar rings to be installed with two N-acetyl (Ac) groups, rare acetamidino (Am), and d-3-hydroxybutyryl (Hb) groups. The strategy for the differentiation of amino groups in trisaccharide 2 will serve well for the syntheses of other complex glycans.

2-Isocyano glucose used in Ugi four-component reaction: An approach to enhance inhibitory effect against DNA oxidation

The Ugi four-component-reaction (Ugi 4CR) allowed synthesizing bisamide from carboxylic acid, aldehyde, amine, and isocyanide in one-pot operation. However, introducing 2-isocyano glucose into the Ugi 4CR and investigating the inhibitory effects of Ugi adducts against radical-induced oxidation of DNA remained technical challenges. We herein applied 2-isocyano glucose (acetylation of hydroxy groups) to perform a catalyst-free Ugi 4CR at room temperature. The gallic, ferulic, caffeic, or p-hydroxybenzoic acids, aniline (or benzylamine and p-aminophenol), and formaldehyde acted as reagents. In the case of inhibiting DNA oxidations induced by 2,2’-azobis(2-amidinopropane hydrochloride) (AAPH), hydroxy radical, and Cu2+/glutathione, the Ugi adduct containing glucose moiety exhibited higher antioxidative activities than the structural analog without glucose moiety involved. It was also proved that high antioxidative property was owing to hydroxy groups in glucose moiety. Therefore, sugar-appended Ugi adducts might hold promising inhibitors for DNA oxidation.

GOLD COMPOSITIONS AND METHODS OF USE THEREOF

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