172587-77-8

Upstream product

• 198193-01-0 tert-Butyl-[(R)-1-((S)-2,2-diethyl-[1,3]dioxolan-4-ylmethyl)-but-3-enyloxy]-diphenyl-silane 
• 127793-60-6 (2R)-1-[(4S)-2,2-diethyl-[1,3]dioxolan-4-yl]-pent-4-en-2-ol 
• 67-56-1 methanol 
• 198192-49-3 (S)-3-(tert-Butyl-diphenyl-silanyloxy)-4-((S)-2,2-diethyl-[1,3]dioxolan-4-yl)-butyraldehyde 

Downstream Products

• 198193-17-8 (S)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (E)-(1S,2S)-4-[(2S,4S,6R)-4-(tert-butyl-diphenyl-silanyloxy)-6-ethoxycarbonylmethyl-6-methoxy-tetrahydro-pyran-2-yl]-1-(1-ethylsulfanylcarbonyl-1-methyl-ethyl)-2-methyl-pent-3-enyl ester 
• 198193-20-3 (R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (E)-(1S,2S)-4-[(2S,4S,6R)-4-(tert-butyl-diphenyl-silanyloxy)-6-ethoxycarbonylmethyl-6-methoxy-tetrahydro-pyran-2-yl]-1-(1-ethylsulfanylcarbonyl-1-methyl-ethyl)-2-methyl-pent-3-enyl ester 
• 172268-63-2 [(2R,4S,6S)-4-(tert-Butyl-diphenyl-silanyloxy)-6-((E)-(S)-1,3-dimethyl-4-triethylsilanyloxy-but-1-enyl)-2-hydroxy-tetrahydro-pyran-2-yl]-acetic acid ethyl ester 
• 172268-53-0 [(2R,4S,6S)-4-(tert-Butyl-diphenyl-silanyloxy)-6-((E)-(3S,4R)-5-ethylsulfanylcarbonyl-4-hydroxy-1,3,5-trimethyl-hex-1-enyl)-2-methoxy-tetrahydro-pyran-2-yl]-acetic acid ethyl ester 
• 172340-04-4 [(2R,4S,6S)-4-(tert-Butyl-diphenyl-silanyloxy)-6-((E)-(3S,4S)-5-ethylsulfanylcarbonyl-4-hydroxy-1,3,5-trimethyl-hex-1-enyl)-2-methoxy-tetrahydro-pyran-2-yl]-acetic acid ethyl ester 
• 172268-56-3 [(2R,4S,6S)-4-(tert-Butyl-diphenyl-silanyloxy)-2-methoxy-6-((1E,7E,13E)-(3S,4R,10R)-1,3,5,5,7-pentamethyl-6-oxo-4,10-bis-triethylsilanyloxy-pentadeca-1,7,13-trienyl)-tetrahydro-pyran-2-yl]-acetic acid ethyl ester 
• 198193-33-8 [(2R,4S,6S)-4-(tert-Butyl-diphenyl-silanyloxy)-6-((1E,7E,13E)-(3S,4R,10R)-6-hydroxy-1,3,5,5,7-pentamethyl-4,10-bis-triethylsilanyloxy-pentadeca-1,7,13-trienyl)-2-methoxy-tetrahydro-pyran-2-yl]-acetic acid ethyl ester 
• 172268-47-2 [(2R,4S,6S)-4-(tert-Butyl-diphenyl-silanyloxy)-2-methoxy-6-((1E,7E)-(3S,4R,10R)-1,3,5,5,7-pentamethyl-6-oxo-4,10-bis-triethylsilanyloxy-pentadeca-1,7-dienyl)-tetrahydro-pyran-2-yl]-acetic acid ethyl ester 
• 198193-30-5 [(2R,4S,6S)-4-(tert-Butyl-diphenyl-silanyloxy)-6-((1E,7E)-(3S,4R,10R)-6-hydroxy-1,3,5,5,7-pentamethyl-4,10-bis-triethylsilanyloxy-pentadeca-1,7-dienyl)-2-methoxy-tetrahydro-pyran-2-yl]-acetic acid ethyl ester 
• 172277-86-0 (7E,13E)-(1R,5R,9R,12S,15S,17S)-17-(tert-Butyl-diphenyl-silanyloxy)-1-methoxy-8,10,10,12,14-pentamethyl-5-((E)-pent-3-enyl)-9-triethylsilanyloxy-4,19-dioxa-bicyclo[13.3.1]nonadeca-7,13-diene-3,11-dione 
• 172268-78-9 (7E,13E)-(1R,5R,9R,12S,15S,17S)-17-(tert-Butyl-diphenyl-silanyloxy)-1-methoxy-8,10,10,12,14-pentamethyl-5-pentyl-9-triethylsilanyloxy-4,19-dioxa-bicyclo[13.3.1]nonadeca-7,13-diene-3,11-dione 
• 172277-84-8 (7E,13E)-(1R,5R,9R,11R,12S,15S,17S)-17-(tert-Butyl-diphenyl-silanyloxy)-11-hydroxy-1-methoxy-8,10,10,12,14-pentamethyl-5-((E)-pent-3-enyl)-9-triethylsilanyloxy-4,19-dioxa-bicyclo[13.3.1]nonadeca-7,13-dien-3-one 
• 172268-49-4 (7E,13E)-(1R,5R,9R,11R,12S,15S,17S)-17-(tert-Butyl-diphenyl-silanyloxy)-11-hydroxy-1-methoxy-8,10,10,12,14-pentamethyl-5-pentyl-9-triethylsilanyloxy-4,19-dioxa-bicyclo[13.3.1]nonadeca-7,13-dien-3-one 
• 172268-77-8 [(2R,4S,6S)-4-(tert-Butyl-diphenyl-silanyloxy)-2-methoxy-6-((1E,7E,13E)-(3S,4R,6R,10R)-4,6,10-trihydroxy-1,3,5,5,7-pentamethyl-pentadeca-1,7,13-trienyl)-tetrahydro-pyran-2-yl]-acetic acid ethyl ester 

Relevant academic research and scientific papers

Total syntheses of (+)-acutiphycin and (+)-trans-20,21-didehydroacutiphycin

The first total syntheses of the cytotoxic macrolides (+)-acutiphycin (1) and (+)-trans-20,21-didehydroacutiphycin (2) have been achieved. An acyclic stereocontrol strategy was employed to establish the configurations at C(5), C(10), and C(13) as well as the E geometry of the C(8,9)-trisubstituted olefin. Importantly, the natural source of 1 and 2, the blue-green alga Osillatoria acutissima, no longer produces these metabolites.

(Tetrahydropyran-2-yl)-aldehydes

Single enanitiomers of 6-(2-hydrocarbyl-substituted ethenyl)-bearing, 4-hydroxy tetrahydro-2H-pyran-2-ones, e.g., 6α-[2-(2-methyl-1-naphthyl)ethenyl]-3,4,5,6-tetrahydro-4β-hydroxy-2H-pyran-2-one (4R,6S) are obtained by a multi-step process which includes