28528-86-1

Usage

Uses

Used in Pharmaceutical Industry:
6-Chloro-6-deoxy-alpha-D-glucopyranose is used as a reactant for the synthesis of 6-chloro-6-deoxy-1,2,3,4-tetra-O-galloyl-alpha-D-glucopyranose, a compound with potential antidiabetic properties. This application is significant as it addresses the growing global concern of diabetes and its associated health complications.
The synthesis of 6-chloro-6-deoxy-1,2,3,4-tetra-O-galloyl-alpha-D-glucopyranose involves the reaction of 6-chloro-6-deoxy-alpha-D-glucopyranose with gallic acid, resulting in a tetragalloyl ester. 6-CHLORO-6-DEOXY-ALPHA-D-GLUCOPYRANOSE has been found to exhibit promising antidiabetic effects, making it a valuable candidate for further research and development in the pharmaceutical industry.

Upstream product

• 492-62-6 alpha-D-glucopyranose 
• 70981-51-0 6-chlorofucose diacetonide 
• 70932-40-0 1,2:3,4-di-O-isopropylidene-6-O-methanesulfonyl-L-galactopyranose 
• 57569-47-8 6-chloro-6-deoxy-1,2-O-isopropylidene-α-D-glucofuranose 3,5-bis(chlorosulfate) 
• 40984-16-5 6,6'-dichloro-6,6'-didesoxysaccharose 
• 57569-50-3 6-chloro-6-deoxy-1,2-O-(1-methylethylidene)-α-D-glucofuranose 

Downstream Products

• 1256381-88-0 C₂₁H₃₃Cl₃N₂O₅ 

Relevant academic research and scientific papers

Difructose dianhydrides from sucrose and fructo-oligosaccharides and their use as building blocks for the preparation of amphiphiles, liquid crystals, and polymers

Controlled selective protonic activation of the fructosyl moiety in sucrose and fructo-oligosaccharides, with pyridinium poly(hydrogen fluoride) at 20°C, yielded either the kinetic product α-Dfructofuranose β-D-fructofuranose 1,2':2,1'-dianhydride (1), or its thermodynamically more stable isomer α-D-fructofuranose β-D-fructopyranose 1,2' :2,1'-dianhydride (2), depending on the hydrogen fluoride-pyridine ratio. A similar reaction was performed with 6,6'-dichloro-6,6'-dideoxysucrose, or 6,6'-dideoxy-6,6'-diiodosucrose, using a slightly higher ratio of HF resulting in the corresponding 6-deoxy-6-halo-α-D-fructofuranose 6'-deoxy-6' -halo-β-D-fructofuranose 1,2':2,1'-dianhydride derivatives. Both 6,6'-dihalides were converted, upon action of the appropriate nucleophile, into the difructofuranose dianhydride derivatives bearing the 6,6'-di-S-heptyl-6,6'-dithio, 6,6'-diazido-6,6'dideoxy and then 6,6'-diamino-6,6'-dideoxy functionalities, 6-Chloro-6-deoxy and 6-deoxy-6-iodo derivatives of 2 were also prepared by direct halogenation, and further converted into the 6-S-heptyl-6-thio, 6-azido-6-deoxy and then 6-amino-6-deoxy derivatives of 2. Reaction of chloromethyloxirane with 1 or 2 yielded hydrophilic polymers. The 6,6'-di-S-heptyl-6,6'-dithio derivative of 1 displayed liquid crystal properties. The 6,6'-dideoxy-6,6'-diiodosucrose precursor was prepared by the reaction of Garegg's iodine-imidazole-triphenylphosphine reagent with sucrose in N,N-dimethylformamide solution. Controlled selective protonic activation of the fructosyl moiety in sucrose and fructo-oligosaccharides, with pyridinium poly(hydrogen fluoride) yielded either the kinetic product α-D-fructofuranose β-D-fructofuranose 1,2′:2,1′-dianhydride (1) or its thermodynamically more stable isomer. Several derivatives were also prepared from a similar reaction with 6,6′-dichloro-6,6′-dideoxysucrose, or 6,6′-dideoxy-6,6′-diiodosucrose. Reaction of chloromethyloxirane with 1 and its isomer gave hydrophilic polymers. The 6,6′-dideoxy-6,6′-diiodosucrose precursor was prepared by the reaction of Garegg's iodine-imidazole-triphenylphosphine reagent with sucrose in N,N-dimethylformamide solution.

THE SYNTHESIS OF CHLORODEOXYHEXOFURANOID DERIVATIVES

The reaction of 1,2-O-isopropylidene-α-D-glucofuranose with sulfuryl chloride at 0 deg C and at 50 deg C afforded 6-chloro-6-deoxy-1,2-O-isopropylidene-α-D-glucofuranose 3,5-bis(chlorosulfate) (3) and 5,6-dichloro-5,6-dideoxy-1,2-O-isopropylidene-β-L-idof

Halogenated L-Fucose and D-Galactose Analogues: Synthesis and Metabolic Effects

Several new analogues of L-fucose modified in the 2-position and the 5-methyl group have been synthesized as potential plasma-membrane glycoconjugate inhibitors or modifiers, and their biological effects have been studied. 2-Chloro-, 2-bromo-, and 2-iodo-2-deoxy-L-fucose (9a, 9b, and 13, respectively) have been prepared by addition of the appropriate halogen to 3,4-di-O-acetyl-L-fucal, followed by hydrolysis of the anomeric halogen and the acetyl groups.A series of four halogenated 5-methyl analogues of L-fucose (4, X = F, Cl, Br and I) have been obtained starting from1,2:3,4-di-O-isopropylidene-L-galactose.The synthesis of this latter compound has been improved.A corresponding series of 6-deoxy-6-halo-D-galactose analogues, which are enantiomers of the 5-(halomethyl)-L-fucose analogues, has also been synthesized.Analogues 4b, 4c, and 9b at 1*10-3 M specifically inhibited the incorporation of L-fucose into macromolecular components of SW613 human mammary tumor cells.Analogue 13 inhibited the growth of L1210 murine leukemic cells with an IC50 of 6*10-5 M in culture. 6-Deoxy-6-fluoro-D-galactose and its enantiomer 4a were found to be effective inhibitors of D-galactose and L-fucose incorporation, respectively, into macromolecular components of human mammary tumor cells.The efectiveness of inhibition was reduced with an increase in size of the halogen atom.Analogue 4a and its enantiomer have been tritiated at C-1 and both were found to be activated to a nucleotide sugar, which was followed by incorporation into the macromolecular fraction of SW613 human mammary tumor cells in vitro.