1315480-00-2

Upstream product

• 617714-97-3 (2R,6S)-2-[(2S,5S,8S)-8,10-bis-(tert-butyldimethylsilanyloxy)-2-methoxy-5-methyl-4-oxodecyl]-6-[2-(4-methoxybenzyloxy)ethyl]-tetrahydropyran-4-one 
• 617715-10-3 (2S,5S,8S)-8,10-bis-(tert-butyldimethylsilanyloxy)-1-{(2S,4S,6S)-4-hydroxy-6-[2-(4-methoxybenzyloxy)ethyl]-tetrahydropyran-2-yl}-2-methoxy-5-methyldecan-4-one 
• 617715-09-0 (2S,6R)-2-[(2R,5S,8S)-8,10-bis-(tert-butyldimethylsilanyloxy)-2-methoxy-5-methyl-4-methylenedecyl]-6-[2-(4-methoxybenzyloxy)ethyl]-4-methylenetetrahydropyran 
• 617714-96-2 (2R,5S,8S)-8,10-bis(tert-butyldimethylsilyloxy)-1-((2S,6R)-6-(2-(4-methoxybenzyloxy)ethyl)-4-methylenetetrahydro-2H-pyran-2-yl)-5-methyl-4-methylenedecan-2-ol 
• 617715-11-4 (2S,5S,8S)-8,10-bis(tert-butyldimethylsilyloxy)-1-((2R,4S,6S)-4-(tert-butyldiphenylsilyloxy)-6-(2-(4-methoxybenzyloxy)ethyl)tetrahydro-2H-pyran-2-yl)-2-methoxy-5-methyldecan-4-one 

Relevant academic research and scientific papers

Studies for the enantiocontrolled preparation of substituted tetrahydropyrans: Applications for the synthesis of leucascandrolide A macrolactone

Strategies for the stereocontrolled preparations of 2,6-cis- and 2,6-trans-substituted tetrahydropyrans have been devised. These studies have explored methodology for asymmetric induction in SE′ reactions using chiral 1,3,2-diazaborolidine controllers. Reactions with aldehydes at -78°C yield nonracemic 1,5-diols for chemoselective internal backside displacements. This concept is developed as a flexible and reliable strategy in studies toward leucascandrolide A macrolactone 2 via the sequential applications of SE′ reactions leading to the C1-C9 aldehyde 14, and the bis-tetrahydropyran 59, respectively.