931095-52-2

Upstream product

• 7226-70-2 (3S,4S,5R,6R)-4-fluoro-6-(hydroxymethyl)tetrahydro-2H-pyran-2,3,5-triol 
• 7226-43-9 [(2R,3R,4S,5S)-3,5,6-triacetoxy-4-fluoro-tetrahydropyran-2-yl]methyl acetate 
• 582-52-5 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 2595-05-3 Diacetone D-glucose 
• 14049-05-9 3-deoxy-1,2;5,6-di-O-isopropylidene-3-fluoro-α-D-glucofuranose 
• 931095-50-0 [(2R,3R,4S,5R,6S)-3,5-diacetoxy-4-fluoro-6-phenylsulfanyl-tetrahydropyran-2-yl]methyl acetate 

Downstream Products

• 931095-55-5 phenyl 4,6-O-benzylidene-3-deoxy-3-fluoro-1-thio-β-D-mannopyranoside 
• 931095-39-5 phenyl 2-O-benzyl-4,6-O-benzylidene-3-deoxy-3-fluoro-1-thio-β-D-mannopyranoside 
• 931095-37-3 phenyl 2-O-benzyl-4,6-O-benzylidene-3-deoxy-3-fluoro-1-thio-β-D-glucopyranoside 

Relevant academic research and scientific papers

Mechanistic Investigation of 1,2-Diol Dehydration of Paromamine Catalyzed by the Radical S-Adenosyl- l -methionine Enzyme AprD4

AprD4 is a radical S-adenosyl-l-methionine (SAM) enzyme catalyzing C3′-deoxygenation of paromamine to form 4′-oxo-lividamine. It is the only 1,2-diol dehydratase in the radical SAM enzyme superfamily that has been identified and characterized in vitro. The AprD4 catalyzed 1,2-diol dehydration is a key step in the biosynthesis of several C3′-deoxy-aminoglycosides. While the regiochemistry of the hydrogen atom abstraction catalyzed by AprD4 has been established, the mechanism of the subsequent chemical transformation remains not fully understood. To investigate the mechanism, several substrate analogues were synthesized and their fates upon incubation with AprD4 were analyzed. The results support a mechanism involving formation of a ketyl radical intermediate followed by direct elimination of the C3′-hydroxyl group rather than that of a gem-diol intermediate generated via 1,2-migration of the C3′-hydroxyl group to C4′. The stereochemistry of hydrogen atom incorporation after radical-mediated dehydration was also established.

AMINOGLYCOSIDES AND USES THEREOF

Provided herein are aminoglycoside compounds, such as compounds of formula (I), (II), (III), (IV), (IVa), (V), (VI), (VIIa), or (VIIb) or pharmaceutically acceptable salts, solvates, stereoisomers, or tautomers of any of the foregoing, useful as therapeutic or prophylactic agents. Also provided herein are methods for their preparation. The compounds may be useful in treating a bacterial infection in a subject, for example a Gram-negative bacterial infection.

MODULAR SYNTHESIS OF AMINOGLYCOSIDES

The present disclosure relates to novel methods for preparing antibacterial aminoglycoside compounds and the compounds used in such preparations.

4,6-O-benzylidene-directed β-mannopyranosylation and α-glucopyranosylation: The 2-deoxy-2-fluoro and 3-deoxy-3-fluoro series of donors and the importance of the O2-C2-C3-O3 interaction

A series of 4,6-O-benzylidene-protected 2-O-benzyl-3-deoxy-3-fluoro- and 3-O-benzyl-2-deoxy-2-fluorogluco-and mannopyranosyl thioglycosides were synthesized and their coupling reactions with a series of alcohols, on preactivation with 1-benzenesulfinylpip