213385-38-7

Upstream product

• 19790-60-4 3-Benzyloxypropanal 
• 158783-76-7 (S)-2-methyl-1-(triisopropylsilyloxy)pentan-3-one 

Downstream Products

• 473759-06-7 Isobutyric acid (1S,2S,3S,4S)-1-(2-benzyloxy-ethyl)-3-hydroxy-2,4-dimethyl-5-triisopropylsilanyloxy-pentyl ester 
• 213385-43-4 (E)-(R)-1-[(4S,5R,6S)-2,2-Di-tert-butyl-5-methyl-6-((S)-1-methyl-2-triisopropylsilanyloxy-ethyl)-[1,3,2]dioxasilinan-4-yl]-8-(4-methoxy-benzyloxy)-6-methyl-oct-2-en-4-one 
• 213385-45-6 (4S,5R,6S)-2,2-Di-tert-butyl-4-[(E)-(4R,6R)-4-methoxy-8-(4-methoxy-benzyloxy)-6-methyl-oct-2-enyl]-5-methyl-6-((S)-1-methyl-2-triisopropylsilanyloxy-ethyl)-[1,3,2]dioxasilinane 
• 213385-44-5 (E)-(4R,6R)-1-[(4S,5R,6S)-2,2-Di-tert-butyl-5-methyl-6-((S)-1-methyl-2-triisopropylsilanyloxy-ethyl)-[1,3,2]dioxasilinan-4-yl]-8-(4-methoxy-benzyloxy)-6-methyl-oct-2-en-4-ol 
• 213385-39-8 (4S,5R,6S)-4-(2-Benzyloxy-ethyl)-2,2-di-tert-butyl-5-methyl-6-((S)-1-methyl-2-triisopropylsilanyloxy-ethyl)-[1,3,2]dioxasilinane 
• 423772-15-0 (2E,4E,14E,20E)-(7R,8R,9R,10R,13S,17R,19R,23S,24R,25S,26S)-9-(tert-Butyl-dimethyl-silanyloxy)-13,19-dimethoxy-8,10,17,24,26-pentamethyl-7-methylsulfanylmethoxy-23,25-bis-triethylsilanyloxy-27-trityloxy-heptacosa-2,4,14,20-tetraenoic acid ethyl ester 
• 423772-12-7 2,2-Dimethyl-propionic acid (10E,16E)-(3R,4R,5R,6R,9S,13R,15R,19S,20R,21S,22S)-5-(tert-butyl-dimethyl-silanyloxy)-9,15-dimethoxy-4,6,13,20,22-pentamethyl-3-methylsulfanylmethoxy-19,21-bis-triethylsilanyloxy-23-trityloxy-tricosa-10,16-dienyl ester 
• 423772-13-8 (10E,16E)-(3R,4R,5R,6R,9S,13R,15R,19S,20R,21S,22S)-5-(tert-Butyl-dimethyl-silanyloxy)-9,15-dimethoxy-4,6,13,20,22-pentamethyl-3-methylsulfanylmethoxy-19,21-bis-triethylsilanyloxy-23-trityloxy-tricosa-10,16-dien-1-ol 
• 423772-14-9 (10E,16E)-(3R,4R,5R,6R,9S,13R,15R,19S,20R,21S,22S)-5-(tert-Butyl-dimethyl-silanyloxy)-9,15-dimethoxy-4,6,13,20,22-pentamethyl-3-methylsulfanylmethoxy-19,21-bis-triethylsilanyloxy-23-trityloxy-tricosa-10,16-dienal 
• 423772-17-2 10-(tert-butyl-dimethyl-silanyloxy)-24-[2-(tert-butyl-dimethyl-silanyloxy)-1,3-dimethyl-4-trityloxy-butyl]-14,20-dimethoxy-9,11,18-trimethyl-8-methylsulfanylmethoxy-oxacyclotetracosa-3,5,15,21-tetraen-2-one 
• 423772-18-3 (3E,5E,15E,21E)-(8R,9R,10R,11R,14S,18R,20R,24S)-10-(tert-Butyl-dimethyl-silanyloxy)-24-[(1R,2S,3S)-2-(tert-butyl-dimethyl-silanyloxy)-1,3-dimethyl-4-trityloxy-butyl]-8-hydroxy-14,20-dimethoxy-9,11,18-trimethyl-oxacyclotetracosa-3,5,15,21-tetraen-2-one 
• 423772-65-0 (3E,5E,15E,21E)-(8R,9R,10R,11R,14S,18R,20R,24S,25R,26S)-10-(tert-Butyl-dimethyl-silanyloxy)-24-hydroxy-14,20-dimethoxy-9,11,18,25-tetramethyl-8-methylsulfanylmethoxy-26-((S)-1-methyl-2-trityloxy-ethyl)-oxacyclohexacosa-3,5,15,21-tetraen-2-one 
• 423772-16-1 (3E,5E,15E,21E)-(8R,9R,10R,11R,14S,18R,20R,24S)-10-(tert-Butyl-dimethyl-silanyloxy)-24-((1S,2S,3S)-2-hydroxy-1,3-dimethyl-4-trityloxy-butyl)-14,20-dimethoxy-9,11,18-trimethyl-8-methylsulfanylmethoxy-oxacyclotetracosa-3,5,15,21-tetraen-2-one 
• 423772-10-5 C₄₆H₆₆O₃SSi₂ 

Relevant academic research and scientific papers

Cytotoxicity and actin-depolymerizing activity of aplyronine A, a potent antitumor macrolide of marine origin, and its analogs

Artificial analogs of aplyronine A (1), a potent antitumor macrolide, were synthesized and structure-activity (cytotoxicity and actin-depolymerizing activity) relationships were investigated; the side-chain in 1 was found to play a key role in both biological activities.

Studies in marine macrolide synthesis: Stereocontrolled synthesis of the C1-C11 and C15-C27 subunits of aplyronine A

The aplyronine C1-C11 subunit 4, containing 4 stereocentres and the (E,E)-diene system, was prepared in 7 steps from ethyl ketone (R)-8 using a boron-mediated anti aldol reaction. The corresponding C15-C27 subunit 5, containing 6 stereogenic centres and an (E)-alkene, was obtained in 10 steps from ketone (S)-14 using a tin(II)-mediated syn aldol reaction and CBS enone reduction.