856410-39-4

Upstream product

• 77-76-9 2,2-dimethoxy-propane 
• 856410-56-5 (E)-(3S,4S)-6-(4-Methoxy-benzyloxy)-1-((S)-4-methyl-3,6-dihydro-2H-pyran-2-yl)-hex-1-ene-3,4-diol 
• 65-85-0 benzoic acid 
• 856410-37-2 (2E,5Z)-(1R)-7-(tert-butyldiphenylsilyl)oxy-1-{(4R,5S)-2,2-dimethyl-5-[2-(4-methoxybenzyloxy)ethyl]-[1,3]-dioxolan-4-yl}-5-methyl-hepta-2,5-dien-1-ol 
• 856410-51-0 Benzoic acid (2E,5Z)-(S)-7-(tert-butyl-diphenyl-silanyloxy)-1-{(4R,5S)-5-[2-(4-methoxy-benzyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-5-methyl-hepta-2,5-dienyl ester 
• 848691-92-9 (Z)-5-(tert-butyldimethylsilyl)oxy-3-methyl-3-penten-1-al 
• 848691-93-0 dimethyl 2-{(4R,5S)-2,2-dimethyl-5-[2-(4-methoxybenzyloxy)ethyl]-[1,3]dioxolan-4-yl}-2-oxo-ethyl-1-phosphonate 
• 856410-50-9 (2E,5Z)-7-(tert-butyldiphenylsilyl)oxy-1-{(4R,5S)-2,2-dimethyl-5-[2-(4-methoxybenzyloxy)ethyl]-[1,3]-dioxolan-4-yl}-5-methyl-hepta-2,5-dien-1-one 
• 172427-68-8 ethyl <2E>-5-(4-methoxybenzyloxy)-2-pentenoate 
• 360768-07-6 (Z)-3-bromo-5-(tert-butyldiphenylsilyl)oxy-1-trimethylsilyl-3-penten-1-yne 
• 848691-96-3 ethyl (2R,3S)-2,3-dihydroxy-5-((4-methoxybenzyl)oxy)pentanoate 
• 848691-97-4 (4R,5S)-ethyl 5-(2-((4-methoxybenzyl)oxy)ethyl)-2,2-dimethyl-1,3-dioxolane-4-carboxylate 
• 848691-95-2 methyl (Z)-5-(tert-butyldimethylsilyl)oxy-3-methyl-3-pentenoate 
• 848691-94-1 (Z)-5-(tert-butyldimethylsilyl)oxy-3-methyl-3-pentenoic acid 

Downstream Products

• 856410-56-5 (E)-(3S,4S)-6-(4-Methoxy-benzyloxy)-1-((S)-4-methyl-3,6-dihydro-2H-pyran-2-yl)-hex-1-ene-3,4-diol 
• 856410-42-9 (E)-(S)-1-[(S)-2-(4-Methoxy-phenyl)-[1,3]dioxan-4-yl]-3-((S)-4-methyl-3,6-dihydro-2H-pyran-2-yl)-prop-2-en-1-ol 
• 856410-59-8 (E)-(3S,4S)-4-(tert-Butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-6-((S)-4-methyl-3,6-dihydro-2H-pyran-2-yl)-hex-5-enal 
• 856410-57-6 tert-Butyl-[(E)-(S)-1-[(S)-2-(4-methoxy-phenyl)-[1,3]dioxan-4-yl]-3-((S)-4-methyl-3,6-dihydro-2H-pyran-2-yl)-allyloxy]-dimethyl-silane 
• 856410-58-7 (E)-(3S,4S)-4-(tert-Butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-6-((S)-4-methyl-3,6-dihydro-2H-pyran-2-yl)-hex-5-en-1-ol 
• 856410-72-5 4-{(2R,6R)-6-[(7E,12E)-(2S,6S,10S,11S)-6,11-Bis-(tert-butyl-dimethyl-silanyloxy)-10-(4-methoxy-benzyloxy)-2-methyl-13-((S)-4-methyl-3,6-dihydro-2H-pyran-2-yl)-4-methylene-trideca-7,12-dienyl]-5,6-dihydro-2H-pyran-2-yl}-but-2-yn-1-ol 
• 856410-69-0 2-(3-{6-[4-(tert-butoxy-diphenyl-silanyloxy)-but-2-ynyl]-3,6-dihydro-2H-pyran-2-yl}-2-methyl-propyl)-9-(tert-butyl-dimethyl-silanyloxy)-8-(4-methoxy-benzyloxy)-11-(4-methyl-3,6-dihydro-2H-pyran-2-yl)-undeca-1,5,10-trien-4-ol 
• 856410-70-3 2-(3-{6-[4-(tert-butoxy-diphenyl-silanyloxy)-but-2-ynyl]-3,6-dihydro-2H-pyran-2-yl}-2-methyl-propyl)-9-(tert-butyl-dimethyl-silanyloxy)-8-(4-methoxy-benzyloxy)-11-(4-methyl-3,6-dihydro-2H-pyran-2-yl)-undeca-1,5,10-trien-4-one 
• 856410-48-5 2-(3-{6-[4-(tert-butoxy-diphenyl-silanyloxy)-but-2-ynyl]-3,6-dihydro-2H-pyran-2-yl}-2-methyl-propyl)-9-(tert-butyl-dimethyl-silanyloxy)-8-(4-methoxy-benzyloxy)-11-(4-methyl-3,6-dihydro-2H-pyran-2-yl)-undeca-1,5,10-trien-4-ol 
• 856410-71-4 C₆₆H₉₈O₈Si₃ 
• 115268-43-4 laulimalide 
• 464914-19-0 (2E,7E)(5S,6S)-6-(tert-butyldimethylsilyloxy)-5-(4-methoxybenzyloxy)-8-((2S)-4-methyl-3,6-dihydro-2H-pyran-2-yl)-octa-2,7-dien-1-ol 
• 478490-93-6 (2E,7E)(5S,6S)-6-(tert-butyldimethylsilyloxy)-5-(4-methoxy-benzyloxy)-8-((2S)-4-methyl-3,6-dihydro-2H-pyran-2-yl)-octa-2,7-dienal 
• 847835-00-1 6-(tert-butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-8-(4-methyl-3,6-dihydro-2H-pyran-2-yl)-octa-2,7-dienoic acid methyl ester 

Relevant academic research and scientific papers

Total synthesis of (-)-laulimalide: Pd-catalyzed stereospecific ring construction of the substituted 3,6-dihydro[2H]pyran units

(Chemical Equation Presented) The potent anticancer agent (-)-laulimalide (1) was prepared through a versatile method that should allow access to other marine natural products. Key steps included a Pd-catalyzed 1,3 chirality transfer of an allylic alcohol

Stereoselective preparation of trisubstituted (Z)-alkenes; synthesis of the C17-C27 fragment of (-)-laulimalide

A Ni-catalyzed cross-coupling reaction of (Z)-5-(tert-butyldiphenylsilyl) oxy-3-bromo-1-trimethylsilyl-3-penten-1-yne (1) with alkyl Grignard reagent gives (Z)-3-alkyl-5-(tert-butyldiphenylsilyl)oxy-1-trimethylsilyl-3-penten-1- ynes (2) stereospecifically

Synthetic approaches towards laulimalide: Synthesis of the C12-C29 fragment

A synthesis of the C12-C29 fragment of laulimalide 1 is described. This synthesis involves the Julia trans-olefination as a key step.