321667-26-9

Upstream product

• 321667-19-0 [(2R,4R,6R)-6-[(S)-3-((2R,3S,6S)-6-Allyl-3-methyl-tetrahydro-pyran-2-yl)-2-hydroxy-propyl]-4-(tert-butyl-diphenyl-silanyloxy)-tetrahydro-pyran-2-yl]-acetic acid methyl ester 
• 321667-21-4 [(2R,4R,6R)-6-[(S)-3-((2R,3S,6S)-6-Allyl-3-methyl-tetrahydro-pyran-2-yl)-2-methoxy-propyl]-4-(tert-butyl-diphenyl-silanyloxy)-tetrahydro-pyran-2-yl]-acetic acid methyl ester 
• 321667-23-6 ((2R,4R,6R)-4-(tert-Butyl-diphenyl-silanyloxy)-6-{(S)-2-methoxy-3-[(2R,3S,6S)-3-methyl-6-(2-oxo-ethyl)-tetrahydro-pyran-2-yl]-propyl}-tetrahydro-pyran-2-yl)-acetic acid methyl ester 
• 617715-12-5 toluene-4-sulfonic acid (1S,2S,5S)-5,7-bis-(tert-butyldimethylsilanyloxy)-1-((S)-3-((2R,4S,6S)-4-(tert-butyldiphenylsilanyloxy)-6-[2-(4-methoxybenzyloxy)ethyl]-tetrahydropyran-2-yl)-2-methoxypropyl)-2-methylheptyl ester 
• 617715-13-6 toluene-4-sulfonic acid (1S,2S,5S)-1-((S)-3-((2R,4S,6S)-4-(tert-butyldiphenylsilanyloxy)-6-[2-(4-methoxybenzyloxy)ethyl]-tetrahydropyran-2-yl)-2-methoxypropyl)-5,7-dihydroxy-2-methylheptyl ester 
• 617715-02-3 acetic acid (R,E)-1-((2S,5S,6R)-6-((S)-3-((2R,4S,6S)-4-(tert-butyldiphenylsilyloxy)-6-(2-(4-methoxybenzyloxy)ethyl)tetrahydro-2H-pyran-2-yl)-2-methoxypropyl)-5-methyltetrahydro-2H-pyran-2-yl)-6-methylhept-3-en-2-yl ester 
• 617715-01-2 (E)-(R)-1-[(2S,5S,6R)-6-((S)-3-((2R,4S,6S)-4-(tert-butyldiphenylsilanyloxy)-6-[2-(4-methoxybenzyloxy)ethyl]-tetrahydropyran-2-yl)-2-methoxypropyl)-5-methyltetrahydropyran-2-yl]-6-methylhept-3-en-2-ol 
• 617715-15-8 (E)-1-[(2S,5S,6R)-6-((S)-3-{(2R,4S,6S)-4-(tert-Butyl-diphenyl-silanyloxy)-6-[2-(4-methoxy-benzyloxy)-ethyl]-tetrahydro-pyran-2-yl}-2-methoxy-propyl)-5-methyl-tetrahydro-pyran-2-yl]-6-methyl-hept-3-en-2-ol 
• 617715-00-1 (E)-1-[(2S,5S,6R)-6-((S)-3-((2R,4S,6S)-4-(tert-butyldiphenylsilanyloxy)-6-[2-(4-methoxybenzyloxy)ethyl]-tetrahydropyran-2-yl)-2-methoxypropyl)-5-methyltetrahydropyran-2-yl]-6-methylhept-3-en-2-one 
• 617715-16-9 acetic acid (R)-(E)-1-((2S,5S,6R)-6-((S)-3-[(2R,4S,6S)-4-(tert-butyldiphenylsilanyloxy)-6-(2-hydroxyethyl)tetrahydropyran-2-yl]-2-methoxypropyl)-5-methyltetrahydropyran-2-ylmethyl)-5-methylhex-2-enyl ester 
• 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 
• 617715-14-7 2-[(2S,5S,6R)-6-((S)-3-((2R,4S,6S)-4-(tert-butyldiphenylsilanyloxy)-6-[2-(4-methoxybenzyloxy)ethyl]-tetrahydropyran-2-yl)-2-methoxypropyl)-5-methyltetrahydropyran-2-yl]-ethanol 
• 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 
• 617714-99-5 2-[(2S,5S,6R)-6-((S)-3-((2R,4S,6S)-4-(tert-butyldiphenylsilanyloxy)-6-[2-(4-methoxybenzyloxy)ethyl]-tetrahydropyran-2-yl)-2-methoxypropyl)-5-methyltetrahydropyran-2-yl]acetaldehyde 

Downstream Products

• 321667-28-1 (1R,3S,5R,7R,9R,13R,15S,18S)-7-(tert-butyldiphenylsilanyloxy)-3-methoxy-18-methyl-13-((E)-4-methylpent-1-enyl)-12,19,20-trioxatricyclo[13.3.1.1^5,9]icosan-11-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.

Formal synthesis of Leucascandrolide A

Asymmetric allylation reactions of stannane-derived allyl diazaborolanes, and the use of the Terashima reagent for the highly selective asymmetric hydride reduction of a β-alkoxy ketone are key features of a highly convergent, stereocontrolled formal synt