1574334-36-3

Upstream product

• 87-72-9 L-(+)-arabinose 
• 92936-93-1 (4R,5S)-4-(bis(ethylthio)methyl)-5-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyl-1,3-dioxolane 
• 22893-94-3 (4R,5S)-4-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyl-5-vinyl-1,3-dioxolane 
• 1574334-59-0 (S)-1-((4S,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl)ethane-1,2-diol 
• 98-59-9 p-toluenesulfonyl chloride 
• 43179-48-2 L-arabinose di(ethylthio)acetal 
• 23568-31-2 2,3:4,5-di-O-isopropylidene-L-arabinose 

Downstream Products

• 1574334-62-5 (E)-benzyl-14-((4S,5R)-2,2-dimethyl-5-((R)-oxiran-2-yl)-1,3-dioxolan-4-yl)tetradec-13-enoate 
• 1574334-65-8 C₄₈H₇₈O₇Si 
• 1574334-69-2 C₄₂H₆₄O₇ 
• 1574334-73-8 C₅₅H₇₇NO₁₀ 
• 1586000-27-2 C₂₂H₃₀O₈ 

Relevant academic research and scientific papers

The first convergent total synthesis of penarolide sulfate A2, a novel α-glucosidase inhibitor

Penarolide sulfate A2, a 31-membered macrolide encompassing a proline residue and three sulfate groups, was firstly synthesized in 16 linear steps with 4.8% overall yield. Three consecutive stereogenic centers in penarolide sulfate A2 were efficiently derived from natural chiral template l-arabinose. The crucial assembly reactions included Brown asymmetric allylation, olefin cross-metathesis, alkyne-epoxide coupling, and macrolactamization. The anti-yeast α-glucosidase activities of penarolide sulfate A2 and its fully desulfated derivative were examined showing IC50 values of 4.87 and 10.74 μg mL-1, respectively.

Stereoselective total synthesis of cochliomycin A

A convergent and stereoselective synthesis of cochliomycin A, a 14-membered resorcyclic acid lactone, based on chiron approach is described. The key reactions involved olefin cross-metathesis and sodium hydride promoted one-pot intramolecular lactonization. l-Arabinose was used as a chiral pool material for the construction of the key fragment.