27108-07-2

Basic information

• Product Name: 4-Fluoro-1-O,2-O,3-O,6-O-tetraacetyl-4-deoxy-β-D-glucopyranose
• Synonyms: 4-Fluoro-1-O,2-O,3-O,6-O-tetraacetyl-4-deoxy-β-D-glucopyranose
• CAS NO: 27108-07-2
• Molecular Formula: C14H19FO9
• Molecular Weight: 350.2936632
• Mol File: 27108-07-2.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 4-Fluoro-1-O,2-O,3-O,6-O-tetraacetyl-4-deoxy-β-D-glucopyranose(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Fluoro-1-O,2-O,3-O,6-O-tetraacetyl-4-deoxy-β-D-glucopyranose(27108-07-2)
• EPA Substance Registry System: 4-Fluoro-1-O,2-O,3-O,6-O-tetraacetyl-4-deoxy-β-D-glucopyranose(27108-07-2)

Safety Data

• Hazardous Substances Data: 27108-07-2(Hazardous Substances Data)

Upstream product

• 30694-44-1 (3R,4R,5S,6R)-5-fluoro-6-(hydroxymethyl)tetrahydro-2H-pyran-2,3,4-triol 
• 108-24-7 acetic anhydride 
• 3601-36-3 methyl 2,3,6-tri-O-benzoyl-α-D-galactopyranoside 
• 56926-53-5 Methyl 4-Deoxy-4-fluoro-α-D-glucopyranoside 
• 84065-98-5 Methyl 2,3,6-Tri-O-benzoyl-4-deoxy-4-fluoro-α-D-glucopyranoside 
• 64-19-7 acetic acid 

Downstream Products

• 109923-29-7 4-deoxy-4-fluoro-α-D-glucopyranosyl  
• 114928-22-2 2',4'-Dinitrophenyl-2,3,6-tri-O-acetyl-4-deoxy-4-fluoro-β-D-glucopyranoside 

Relevant articles and documents

5-FLUORO-C-(ARYL OR HETEROCYCLYL)-GLYCOSIDE DERIVATIVES USEFUL AS DUAL SGLT1 / SGLT2 MODULATORS

The present invention is directed to 5-fluoro-C-(aryl or hetercyclyl)-glycoside derivatives, pharmaceutical compositions containing them and their use in the treatment of disorders and conditions modulated by SGLT activity, more particularly dual SGLT1/2 activity.

Synthesis of UDP-4-deoxy-4-fluoroglucose and UDP-4-deoxy-4-fluorogalactose and their interactions with enzymes of nucleotide sugar metabolism

Fluorinated carbohydrates can be used as probes of enzymatic active sites. We report the synthesis of 4-deoxy-4-fluoro-α-D-galactose-1-phosphate and the substrate analogues of UDP-galactose, UDP4-deoxy-4-fluoro-α-D-galactose (UDP-FGal), and of UDP-glucose, UDP-4-deoxy-4-fluoro-α-D-glucose (UDP-FGlc), which may be useful in analyzing the binding properties of enzymes that utilize nucleotide sugars as substrates. As a first step in this study, we determine the kinetic and inhibition parameters for UDP-FGal and UDP-FGlc interacting with UDP-glucose dehydrogenase and UDP-galactose 4-epimerase. UDP-FGlc is a substrate for bovine liver UDP-glucose dehydrogenase: K(m) = 30.2 ± 4.5 μM slightly higher than the value 9.6 ± 0.7 μM for UDP-glucose, and V(m)(UDP-FGlc) = 0.46V(mUDP-Glc). UDP-FGal is not a substrate for UDP-glucose dehydrogenase but is a competitive inhibitor with respect to UDP-glucose (K(i) = 19.9 ± 6.6 μM). These analogs also bind to UDP-galactose 4-epimerase from E. coli with dissociation constants K(d) of 1.4 and 1.1 mM for UDP-FGlc and UDP-FGal, respectively.