6304-86-5

Usage

Uses

Used in Medicinal Chemistry:
6-deoxy-6-iodohexopyranose is used as a building block for the development of iodine-labeled molecules for various imaging and diagnostic purposes.
Used in Molecular Imaging and Diagnostic Medicine:
6-deoxy-6-iodohexopyranose is used as a valuable tool for radioimaging studies, particularly with radioactive isotopes of iodine such as iodine-131 for thyroid imaging and iodine-123 for brain and heart imaging.

Upstream product

• 82867-69-4 6,6’-dideoxydiiodosucrose 
• 5155-46-4 methyl 6-iodo-6-deoxy-α-D-glucopyranoside 
• 194029-99-7 (2S,3S,4S,5R)-2-Iodomethyl-6-methoxy-tetrahydro-pyran-3,4,5-triol 
• 70932-40-0 1,2:3,4-di-O-isopropylidene-6-O-methanesulfonyl-L-galactopyranose 
• 70981-53-2 (3aS,5R,5aS,8aR,8bS)-5-(iodomethyl)-2,2,7,7-tetramethyltetrahydro-3aH-bis [1,3]dioxolo[4,5-b:4′5′-d]pyran 
• 95720-92-6 1,2,3,4-tetra-O-acetyl-6-deoxy-6-iodo-D-glucopyranose 
• 57-50-1 Sucrose 

Downstream Products

• 24871-54-3 acetoxy α-D-2,3,4-triacetoxy-6-deoxy-6-iodoglucopyranoside 

Relevant academic research and scientific papers

NOVEL 15O-LABELED MONOSACCHARIDE AND PRODUCING METHOD THEREOF

This invention relates to novel 15O-labeled monosaccharide useful for positron emission tomography (PET) and producing method thereof.

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.

FACILE PREPARATION OF DEOXYIODOCELLULOSE AND ITS CONVERSION INTO 5,6-CELLULOSENE

Treatment of 6-chloro-6-deoxycellulose with sodium iodide in 2,5-hexanedione gave 6-deoxy-6-iodocellulose; > 80 percent of the chlorine atoms were replaced. 6-Deoxy-6-iodo-D-glucose was identified by g.l.c.-m.s. in hydrolyzates of deoxyiodocellulose.Acetylated 6-deoxy-6-iodocellulose was converted almost quantitatively into 5,6-cellulosene acetate, wich was characterized by hydrolyzing the product and converting the resultant dicarbonyl sugar into an isopropylidene acetal 10.The changes of molecular-weight distribution during iodination and dehydroiodination were investigated by gel-permeation chromatography.

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.