38711-37-4

Basic information

• Product Name: b-D-Glucopyranose, 2-deoxy-2-fluoro-
• Synonyms: NSC240588
• CAS NO: 38711-37-4
• Molecular Formula: C₆H₁₁FO₅
• Molecular Weight: 182.1469
• Mol File: 38711-37-4.mol
• Article Data: 21

Chemical Properties

• Boiling Point: 413.6°Cat760mmHg
• Flash Point: 186.3°C
• Density: 1.59g/cm³
• CAS DataBase Reference: b-D-Glucopyranose, 2-deoxy-2-fluoro-(CAS DataBase Reference)
• NIST Chemistry Reference: b-D-Glucopyranose, 2-deoxy-2-fluoro-(38711-37-4)
• EPA Substance Registry System: b-D-Glucopyranose, 2-deoxy-2-fluoro-(38711-37-4)

Safety Data

• Hazardous Substances Data: 38711-37-4(Hazardous Substances Data)

Usage

General Description

B-D-Glucopyranose, 2-deoxy-2-fluoro- is a modified form of the sugar molecule glucose, where the hydroxyl group at the second carbon is replaced with a fluorine atom. This modification confers unique properties to the molecule, making it resistant to degradation by enzymes and allowing it to be used as a tracer in positron emission tomography (PET) imaging studies. Its modified structure also makes it a useful tool in studying the metabolism and uptake of glucose in various biological systems, as well as in the development of new pharmaceuticals and imaging agents.

Upstream product

• 141395-48-4 1,3,4,6-tetra-O-acetyl-2-deoxy-2-fluoro-α/β-D-glucopyranoside 
• 1326775-51-2 1-(2-(trimethylsilyl)ethyl)-2-deoxy-3-O-ethoxymethyl-2-fluoro-4,6-O-isopropylidene-β-D-glucopyranoside 
• 95519-65-6 methyl 3,4,6-tri-O-acetyl-2-deoxy-2-fluoro-β-D-mannopyranoside 
• 95519-67-8 methyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-fluoro-β-D-mannopyranoside 
• 95519-62-3 methyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-fluoro-α-D-mannopyranoside 
• 20750-03-2 methyl 3-O-acetyl-4,6-O-benzylidene-β-D-glucopyranoside 
• 129706-93-0 methyl 3-O-benzyl-4,6-O-benzylidene-β-D-glucopyranoside 
• 2774-19-8 methyl 3-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside 
• 20771-15-7 methyl 3,4,6-tri-O-acetyl-β-D-glucopyranoside 
• 95519-63-4 methyl 3-O-acetyl-4,6-O-benzylidene-2-deoxy-2-fluoro-β-D-mannopyranoside 
• 21193-75-9 D-galactal 
• 13265-84-4 D-glucal 
• 86783-82-6 2-fluoro-D-glucose 
• 4098-06-0 triacetyl-D-galactal 

Downstream Products

• 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 
• 7226-42-8 1,3,4,6-tetra-O-acetyl-2-deoxy-2-fluoro-α-D-glucopyranose 
• 1563187-70-1 C₁₉H₁₉FN₂O₅S 
• 67341-46-2 guanosine-5’-diphospho-2′′-fluoro-α-D-mannopyranosyl 
• 146-91-8 guanosine-5'-diphosphate 
• 67341-44-0 uridine 5'-diphospho-2-fluoro-2-deoxy-α-D-mannopyranoside 
• 7226-42-8 1,3,4,6-tetra-O-acetyl-2-deoxy-2-fluoro-α-D-galactopyranose 
• 7226-42-8 1,3,4,6-tetra-O-acetyl-2-deoxy-2-fluoro-α-D-mannopyranoside 

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.