162808-24-4

Upstream product

• 71-43-2 benzene 
• 7306-64-1 2,3,5,6-di-O-isopropylidene-D-mannono-1,4-lactone 
• 591-51-5 phenyllithium 
• 14131-84-1 2,3:5,6-di-O-isopropylidene-α-D-mannofuranose 
• 119842-22-7 2,3:5,6-di-O-isopropylidene-1-C-phenyl-D-mannofuranoside 
• 162808-23-3 (3aS,4R,6S,6aR)-4-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyl-6-phenyltetrahydrofuro[3,4-d][1,3]dioxole 

Downstream Products

• 162630-69-5 Z-(C-phenyl 5,6-dideoxy-2-O-trifluoromethanesulphonyl-α-D-lyxo-heptofuranosi)uro-5-enono-3,7-lactone 
• 119842-24-9 Propionic acid (2S,3S,3aS,7aR)-5-oxo-2-phenyl-3,3a,5,7a-tetrahydro-2H-furo[3,2-b]pyran-3-yl ester 
• 120019-23-0 (-)-7-epi-altholactone 
• 114488-17-4 (-) Altholactone 

Relevant academic research and scientific papers

Synthesis and biological evaluation of flexible and conformationally constrained LpxC inhibitors

Inhibitors of the UDP-3-O-[(R)-3-hydroxymyristoyl]-N-acetylglucosamine deacetylase (LpxC) represent promising candidates for the development of antibiotics possessing a so far unexploited mechanism of action. In a chiral pool synthesis, starting from the d-mannose derived mannonolactone 4, conformationally constrained C-glycosidic as well as open chained hydroxamic acids with a defined stereochemistry were prepared. Diversity was introduced by performing C-C coupling reactions like the Sonogashira and Suzuki cross-coupling reactions. The biological evaluation of the synthesized compounds revealed that in the case of the C-glycosides a long, linear and rigid hydrophobic side chain is required for antibiotic activity against E. coli. The open chain derivatives show higher biological activity than the conformationally constrained C-glycosides. The morpholinomethyl substituted open chain derivative 43, being the most potent compound presented in this paper, inhibits LpxC with a K i value of 0.35 μM and represents a promising lead structure. The Royal Society of Chemistry.

Stereocontrolled synthesis of four diastereomeric C-aryl manno- and talofuranosides

In a chiral-pool synthesis starting from d-mannono-1,4-lactone 1a, the four diastereomeric C-aryl furanosides (1S,4R)-4a, (1S,4S)-4b, (1R,4R)-4c, and (1R,4S)-4d were obtained in a stereocontrolled manner. The key steps of the synthetic pathway comprise a

Enantiospecific Synthesis of (+)-Altholactone and its Three Stereoisomers

(+)-Altholactone 1 and (+)-7-epi-altholactone 3 were constructed from D-gulonolactone whereas their respective enantiomers (-)-altholactone 2 and (-)-7-epi-altholactone 4 were synthesized from D-mannose, involving stereocontrolled reduction of the lactols 21 as a key step.

Enantiospecific Syntheses of (+)- and (-)-Altholactone (Goniothalenol)

(+)-Altholactone (1) and its enantiomer (2) have been synthesised from D-gulolactone and D-mannose, respectively, with stereocontrolled reduction (Et3SiH/BF3.Et2O) of the lactols (4) and (10) as a key step.