243468-89-5

Upstream product

• 558-13-4 carbon tetrabromide 
• 243468-87-3 (3S,4S,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-6-(4-methoxy-benzyloxy)-3,5-dimethyl-hexanal 
• 209251-26-3 (2R,3R,4R)-1-[(para-methoxybenxyl)oxy]-2,4-dimethyl-3-hexanol 
• 69739-34-0 t-butyldimethylsiyl triflate 
• 1613397-64-0 C₂₈H₄₄O₆SSi 
• 1216963-74-4 lithium acetylide-ethylenediamine complex 
• 1613397-61-7 C₃₀H₄₄O₆Si 
• 1613397-63-9 C₂₁H₃₆O₄Si 
• 1613397-56-0 C₂₄H₃₀O₆ 
• 1613397-57-1 C₂₁H₃₈O₄Si 
• 160238-46-0 (2R)-3-(4-methoxybenzyloxy)-2-methyl-1-propanal 
• 243468-88-4 tert-Butyl-{(1S,2S)-5,5-dibromo-1-[(R)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-2-methyl-pent-4-enyloxy}-dimethyl-silane 
• 209251-62-7 (2R,3S,4S)-1-[(para-methoxybenxyl)oxy]-2,4-dimethyl-3-hexanol 
• 243468-76-0 (3S,4S,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-6-(4-methoxy-benzyloxy)-3,5-dimethyl-hexan-1-ol 

Downstream Products

• 442899-68-5 (2Z,4E,10E,12E)-(6R,7S,8S,14S,15R,16S,17S,18R,19R)-17-(tert-Butyl-dimethyl-silanyloxy)-19-(3,4-dimethoxy-benzyloxy)-7-hydroxy-2,14-dimethoxy-4,6,8,10,16,18-hexamethyl-15-triethylsilanyloxy-icosa-2,4,10,12-tetraenoic acid methyl ester 
• 88899-55-2 bafilomycin A₁ 

Relevant academic research and scientific papers

Modification of bafilomycin structure to efficiently synthesize solid-state NMR probes that selectively bind to vacuolar-type ATPase

Bafilomycin (Baf) is one of the most potent inhibitors of vacuolar-type ATPase, which is strongly implicated in age-related diseases. However, the binding site of the antibiotic on the protein remains unclear because of the complexity of the structure of Baf bound to the target subunit in the transmembrane region. For conducting structural studies by applying solid-state NMR, which is one of the most promising methodologies available for structural analysis in membrane system, preparing bioactive fluorinated Baf analogues is essential. In this study two Baf analogues were carefully designed and efficiently synthesized through the convergent coupling of three segments. Biological evaluation revealed that the activity of 24-F-Baf was comparable to that of Baf, indicating its utility as a potential probe for solid-state NMR analysis. By contrast, desmethylated 24-F-Baf exhibited markedly diminished activity. The absence of two methyl groups caused a critical conformational change in the macrocyclic core structure necessary for binding to the target protein.

Design and synthesis of 24-fluorinated bafilomycin analogue as an NMR probe with potent inhibitory activity to vacuolar-type ATPase

A fluorine-labeled bafilomycin analogue was designed and convergently synthesized from three segments via the Stille coupling, macrolactonization, and diastereoselective aldol reaction. The V-ATPase inhibitory activity of the analogue was comparable to that of the natural product, indicating its utility as a potential molecular probe for investigating the inhibition mechanism of bafilomycin by NMR.

Total synthesis of (-)-bafilomycin A1

A highly stereoselective total synthesis of (-)-bafilomycin A1, the naturally occurring enantiomer of this potent vacuolar ATPase inhibitor, is described. The synthesis features the highly stereoselective aldol reaction of methyl ketone 8b and