7226-39-3

Basic information

• Product Name: 2-FLUORO--ALFA-D-2-DEOXY-GLUCOSE
• Synonyms: 2-FLUORO--ALFA-D-2-DEOXY-GLUCOSE;3-Fluoro-6-hydroxymethyl-tetrahydro-pyran-2,4,5-triol
• CAS NO: 7226-39-3
• Molecular Formula: C₆H₁₁FO₅
• Molecular Weight: 0
• Mol File: 7226-39-3.mol
• Article Data: 20

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-FLUORO--ALFA-D-2-DEOXY-GLUCOSE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-FLUORO--ALFA-D-2-DEOXY-GLUCOSE(7226-39-3)
• EPA Substance Registry System: 2-FLUORO--ALFA-D-2-DEOXY-GLUCOSE(7226-39-3)

Safety Data

• Hazardous Substances Data: 7226-39-3(Hazardous Substances Data)

Usage

Description

2-FLUORO--ALFA-D-2-DEOXY-GLUCOSE, also known as 2-Deoxy-2-fluoro-D-galactose, is a deoxyfluoro sugar that serves as an essential building block in the synthesis of various complex carbohydrates and related compounds. Its unique structure, featuring a fluorine atom in place of a hydroxyl group, imparts distinct chemical and biological properties that make it valuable in a range of applications.

Uses

Used in Pharmaceutical and Biochemical Research:
2-FLUORO--ALFA-D-2-DEOXY-GLUCOSE is used as an intermediate in the synthesis of complex carbohydrates and related compounds for pharmaceutical and biochemical research. Its unique structure allows for the development of novel therapeutic agents and diagnostic tools.
Used in Organic Synthesis:
In the field of organic synthesis, 2-FLUORO--ALFA-D-2-DEOXY-GLUCOSE is used as a key precursor for the preparation of other deoxyfluoro sugars, such as 2-deoxy-2-fluoro-D-altrose, 2-deoxy-2-fluoro-D-allose, and 3-deoxy-3-fluoro-D-glucose. These compounds have potential applications in various industries, including pharmaceuticals, diagnostics, and materials science.
Used in Drug Development:
2-FLUORO--ALFA-D-2-DEOXY-GLUCOSE is utilized in drug development as a potential therapeutic agent or as a building block for the creation of new pharmaceutical compounds. Its unique chemical properties may contribute to the development of drugs with improved efficacy and selectivity.
Used in Diagnostic Imaging:
In diagnostic imaging, 2-FLUORO--ALFA-D-2-DEOXY-GLUCOSE may be used as a contrast agent or in the development of imaging probes. The presence of the fluorine atom can enhance imaging capabilities, providing clearer and more detailed images for medical diagnosis.
Used in Materials Science:
2-FLUORO--ALFA-D-2-DEOXY-GLUCOSE can also be employed in materials science for the development of new materials with unique properties. The incorporation of fluorine into the sugar structure may lead to materials with improved stability, reactivity, or other desirable characteristics.

InChI:InChI=1/2C7H11NO3S.C6H12NO.C6H8NO.Co/c2*9-7-5-3-1-2-4-6(5)12(10,11)8-7;2*8-5-6-3-1-2-4-7-6;/h2*5-6H,1-4H2,(H,8,9);6,8H,1-5H2;1-3,8H,4-5H2;/q;;2*-1;+3/p-1

Upstream product

• 24679-92-3 3,4,6-tri-O-acetyl-2-deoxy-2-fluoro-β-D-mannosyl fluoride 
• 86783-82-6 2-fluoro-D-glucose 
• 13265-84-4 D-glucal 
• 63598-36-7 4,6-O-benzylidene-D-glucal 
• 140681-55-6 Selectfluor 
• 140681-68-1 1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(trifluoromethanesulfonate) 
• 2873-29-2 D-glucal triacetate 
• 141395-49-5 [(2R,3R,4S,5S)-3,4,6-triacetoxy-5-fluoro-tetrahydropyran-2-yl]methyl acetate 
• 7226-39-3 2-deoxy-2-fluoro-D-mannopyranoside 
• 7226-42-8 1,3,4,6-tetra-O-acetyl-2-deoxy-2-fluoro-α-D-glucopyranose 
• 141395-48-4 1,3,4,6-tetra-O-acetyl-2-deoxy-2-fluoro-α/β-D-glucopyranoside 
• 115216-41-6 methyl 4,6-O-benzylidene-2-deoxy-2-fluoro-α-D-glucopyranoside 
• 1326775-51-2 1-(2-(trimethylsilyl)ethyl)-2-deoxy-3-O-ethoxymethyl-2-fluoro-4,6-O-isopropylidene-β-D-glucopyranoside 
• 1326775-48-7 (2-(trimethylsilyl)ethyl) 3-O-ethoxymethyl-4,6-O-isopropylidene-2-O-(1,1,2,2-tetrafluoro-2-(6-carboxy-1,1,2,2-tetrafluorohexyloxy)ethanesulfonyl)-β-D-mannopyranoside 

Downstream Products

• 31077-91-5 1,3,4,6-tetra-O-acetyl-2-deoxy-2-fluoro-β-D-mannopyranose 
• 7226-42-8 1,3,4,6-tetra-O-acetyl-2-deoxy-2-fluoro-α-D-mannopyranoside 
• 38711-37-4 2-deoxy-2-fluoro-β-D-glucopyranose 
• 7226-39-3 2-fluoro-2-deoxy-D-glucose 
• 176977-70-1 α-2-fluoro-2-deoxymannose-6-phosphate 
• 99257-08-6 α-2-fluoro-2-deoxyglucose-6-phosphate 
• 176977-71-2 β-2-fluoro-2-deoxymannose-6-phosphate 
• 99257-09-7 β-2-fluoro-2-deoxyglucose-6-phosphate 
• 141395-59-7 (R)-3-Benzyloxy-tetradecanoic acid (2R,4aR,6R,7S,8S,8aR)-6-(bis-benzyloxy-phosphoryloxy)-7-fluoro-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester 
• 141395-60-0 (R)-3-Tetradecanoyloxy-tetradecanoic acid (2R,4aR,6R,7S,8S,8aR)-6-(bis-benzyloxy-phosphoryloxy)-7-fluoro-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester 
• 141395-55-3 Phosphoric acid dibenzyl ester (2R,4aR,6S,7S,8S,8aS)-7-fluoro-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl ester 
• 141395-54-2 Phosphoric acid dibenzyl ester (2R,4aR,6R,7S,8S,8aS)-7-fluoro-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl ester 
• 7226-42-8 1,3,4,6-tetra-O-acetyl-2-deoxy-2-fluoro-α-D-glucopyranose 
• 7226-42-8 1,3,4,6-tetra-O-acetyl-2-deoxy-2-fluoro-α-D-galactopyranose 

Relevant articles and documents

Addressing the Structural Complexity of Fluorinated Glucose Analogues: Insight into Lipophilicities and Solvation Effects

In this work, we synthesized all mono-, di-, and trifluorinated glucopyranose analogues at positions C-2, C-3, C-4, and C-6. This systematic investigation allowed us to perform direct comparison of 19F resonances of fluorinated glucose analogues and also to determine their lipophilicities. Compounds with a fluorine atom at C-6 are usually the most hydrophilic, whereas those with vicinal polyfluorinated motifs are the most lipophilic. Finally, the solvation energies of fluorinated glucose analogues were assessed for the first time by using density functional theory. This method allowed the log P prediction of fluoroglucose analogues, which was comparable to the C log P values obtained from various web-based programs.

Solid-supported reagents composed of a copolymer possessing 2-O-sulfonyl mannosides and phase-transfer catalysts for the synthesis of 2-fluoroglucose

We described the synthesis of a solid-supported co-polymer possessing mannosides and phase-transfer catalysts and synthesis of 2-fluoroglucoside from it. We first prepared a soluble copolymer from two allene monomers possessing a precursor for the synthesis of 2-fluoroglycose and a crown ether. The copolymerization of the monomers via the π-ally nickel-catalyst smoothly proceeded at room temperature to provide a desired copolymer without decomposition of the sulfonate esters. The copolymer exhibited high reactivity towards fluorination in comparison with a conventional precursor. We next synthesized the solid-supported copolymer by using the solid-supported initiator attached with TentaGel resins. TentaGel enabled polymerization under stirring with stirring bar without decomposition. The solid-supported copolymer exhibited comparable reactivity towards fluorination in comparison with the soluble copolymer. In addition, it can be easily separated from the reaction vessel by filtration.

Sialidase substrate specificity studies using chemoenzymatically synthesized sialosides containing C5-modified sialic acids

para-Nitrophenol-tagged sialyl galactosides containing sialic acid derivatives in which the C5 hydroxyl group of sialic acids was systematically substituted with a hydrogen, a fluorine, a methoxyl or an azido group were successfully synthesized using an efficient chemoenzymatic approach. These compounds were used as valuable probes in high-throughput screening assays to study the importance of the C5 hydroxyl group of sialic acid in the recognition and the cleavage of sialoside substrates by bacterial sialidases.