24871-54-3

Usage

General Description

6-Deoxy-6-iodo-α-D-glucopyranose 1,2,3,4-tetraacetate is a chemical compound derived from glucose. It is a tetraacetate derivative of 6-iodo-α-D-glucopyranose, where all the hydroxyl groups of glucose are replaced by acetate groups. The presence of the iodine atom at the 6th position of the glucose ring makes 6-Deoxy-6-iodo-α-D-glucopyranose 1,2,3,4-tetraacetate unique. It has potential applications in organic synthesis and medicinal chemistry due to its specific structure and properties. Additionally, its derivatives may be used as intermediates in the production of various pharmaceuticals and agrochemicals.

InChI:InChI=1/C14H19IO9/c1-6(16)20-11-10(5-15)24-14(23-9(4)19)13(22-8(3)18)12(11)21-7(2)17/h10-14H,5H2,1-4H3

Upstream product

• 7404-34-4 1,2,3,4-Tetra-O-acetyl-6-bromo-6-deoxy-α-D-glucopyranose 
• 6304-86-5 6-iodo-D-6-deoxy-glucose 
• 108-24-7 acetic anhydride 
• 29581-38-2 2,3,4-tri-O-acetyl-6-bromo-6-deoxy-α-D-glucopyranosyl bromide 
• 57-50-1 Sucrose 
• 82867-69-4 6,6’-dideoxydiiodosucrose 
• 5155-46-4 methyl 6-iodo-6-deoxy-α-D-glucopyranoside 
• 97-30-3 methyl-alpha-D-glucopyranoside 
• 6304-96-7 methyl 2,3,4-tri-O-acetyl-6-deoxy-6-iodo-α-D-glucopyranoside 
• 20113-43-3 1,2,3,4-tetra-O-acetyl-6-O-p-tolylsulfonyl-α-D-glucopyranose 

Downstream Products

• 50692-56-3 6-Desoxy-6-iod-2,3,4-tri-O-acetyl-α-D-glucopyranosylbromid 

Relevant academic research and scientific papers

An efficient and cost-effective preparation of di-O-acetyl-d-rhamnal

We have developed a synthetic route to the frequently utilized deoxysugar building block di-O-acetyl-d-rhamnal originating from the inexpensive starting material methyl α-d-glucopyranoside. Our approach proceeds in five steps with minimal column chromatography purification needed to afford the title compound in good overall yield.

A General Synthesis of Iminosugars

1-Deoxynojirimycin, 1-deoxymannojirimycin, and 1-deoxygalactostatin have been synthesized by epoxidation of tri-O-acetyl-6-deoxyhex-5-enopyranosyl azides followed by methanolysis, deacetylation, and catalytic hydrogenation. 1,6-Dideoxygalactostatin was obtained by the reaction of 2,3,4-tri-O-acetyl-6-deoxy-β-L-arabino-hex-5-enopyranosyl azide with NIS in methanol followed by deacetylation and catalytic hydrogenation. The overall yields were 4.4-23.5% over seven to nine steps.

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.