174474-74-9

Upstream product

• 67-56-1 methanol 
• 174589-62-9 (2aR,4S,4aS,6R,8aS,8bS)-8b-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-6-hydroxy-4a-methyl-octahydro-2-oxa-cyclobuta[a]naphthalen-7-one 
• 155681-67-7 (4'aS,5'S,7'S,8'S,8'aS)-5'-(tert-Butyl-dimethyl-silanyloxy)-8'-hydroxymethyl-4'a-methyl-octahydro-spiro[[1,3]dioxolane-2,2'-naphthalene]-7',8'-diol 
• 174474-72-7 Trifluoro-methanesulfonic acid (4'aS,5'S,7'S,8'S,8'aS)-5'-(tert-butyl-dimethyl-silanyloxy)-8'-hydroxy-4'a-methyl-8'-trimethylsilanyloxymethyl-octahydro-spiro[[1,3]dioxolane-2,2'-naphthalen]-7'-yl ester 
• 174589-61-8 Trifluoro-methanesulfonic acid (4'aS,5'S,8'aS)-5'-(tert-butyl-dimethyl-silanyloxy)-4'a-methyl-3',4',4'a,5',6',8'a-hexahydro-1'H-spiro[[1,3]dioxolane-2,2'-naphthalen]-8'-yl ester 
• 168421-57-6 C₂₇H₄₂O₅Si 
• 168421-83-8 (2aR,4S,4aS,8aS,8bS)-8b-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-4a-methyl-octahydro-2-oxa-cyclobuta[a]naphthalen-7-one 
• 155681-66-6 [(4'aS,5'S,8'aR)-5'-(tert-Butyl-dimethyl-silanyloxy)-4'a-methyl-3',4',4'a,5',6',8'a-hexahydro-1'H-spiro[[1,3]dioxolane-2,2'-naphthalen]-8'-yl]-methanol 
• 155681-64-4 (4'aS,5'S,8'aS)-5'-(tert-Butyl-dimethyl-silanyloxy)-4'a-methyl-octahydro-spiro[[1,3]dioxolane-2,2'-naphthalen]-8'-one 
• 155681-68-8 C₂₀H₃₆O₅Si 
• 100-39-0 benzyl bromide 
• 69739-34-0 t-butyldimethylsiyl triflate 
• 878-47-7 (4aS,5S)-4,4a,5,6,7,8-hexahydro-5-hydroxy-4a-methylnaphthalen-2(3H)-one 
• 155681-65-5 (4'aS,5'S,8'aS)-5'-(tert-Butyl-dimethyl-silanyloxy)-4'a-methyl-3',4',4'a,5',6',8'a-hexahydro-1'H-spiro[[1,3]dioxolane-2,2'-naphthalene]-8'-carboxylic acid methyl ester 

Downstream Products

• 155588-13-9 (2aR,4S,4aS,6R,11S,12S,12aR,12bS)-12-benzoyloxy-11-hydroxy-4a,8,13,13-tetramethyl-5-oxo-4-triethylsilyloxy-3,4,4a,5,6,9,10,11,12,12a-decahydro-1H-7,11-methanocyclodeca[3,4]benzo[1,2-b]oxete-6,12b(2aH)diyl diacetate 
• 168421-62-3 [(1S,2S,3S,4S,6R)-1-Benzyloxy-3-(2,2-dimethoxy-ethyl)-3-methyl-2-vinyl-7-oxa-bicyclo[4.2.0]oct-4-yloxy]-tert-butyl-dimethyl-silane 
• 168421-84-9 2-[(1S,2S,3S,4S,6R)-1-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-3-(2,2-dimethoxy-ethyl)-3-methyl-7-oxa-bicyclo[4.2.0]oct-2-yl]-ethanol 
• 168421-63-4 (1S,2S,3S,4S,6R)-1-(benzyloxy)-4-(tert-butyldimethylsilyloxy)-3-(2,2-dimethoxyethyl)-3-methyl-7-oxabicyclo[4.2.0]octane-2-carbaldehyde 
• 168421-74-7 C₂₉H₃₆O₆ 
• 168421-65-6 5-{(S)-[(1S,2R,3S,4S,6R)-1-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-3-(2,2-dimethoxy-ethyl)-3-methyl-7-oxa-bicyclo[4.2.0]oct-2-yl]-hydroxy-methyl}-2,6,6-trimethyl-cyclohexa-2,4-dienone 
• 168421-67-8 (S)-5-{(S)-[(1S,2R,3S,4S,6R)-1-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-3-(2,2-dimethoxy-ethyl)-3-methyl-7-oxa-bicyclo[4.2.0]oct-2-yl]-hydroxy-methyl}-5-hydroxy-2,6,6-trimethyl-cyclohex-2-enone 
• 168421-76-9 C₃₅H₅₀O₇Si 
• 168421-73-6 C₃₅H₅₀O₆Si 
• 168421-75-8 C₃₅H₅₀O₆Si 
• 168421-81-6 C₃₅H₅₀O₈Si 
• 168421-68-9 (4S,5S)-4-[(1S,2R,3S,4S,6R)-1-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-3-(2,2-dimethoxy-ethyl)-3-methyl-7-oxa-bicyclo[4.2.0]oct-2-yl]-6,6,8-trimethyl-1,3-dioxa-spiro[4.5]dec-8-ene-2,7-dione 
• 168421-79-2 C₃₆H₅₂O₈Si 
• 168421-69-0 (4S,5S)-4-[(1S,2R,3S,4S,6R)-1-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-3-(2,2-dimethoxy-ethyl)-3-methyl-7-oxa-bicyclo[4.2.0]oct-2-yl]-6,6,8-trimethyl-1,3-dioxa-spiro[4.5]decane-2,7-dione 

Relevant academic research and scientific papers

Total synthesis of baccatin III and taxol

An intramolecular Heck reaction (90 → 91) serves as the key step in the total synthesis of the titled compounds. The synthetic route is based on utilizing the Wieland-Miescher ketone (5) as a matrix to provide the C and D rings of the targets and to provide functionality implements for joining this sector to an A ring precursor (6). Catalytically induced enantiotopic control and early emplacement of the oxetane are other features of the route.

Eine Totalsynthese von Taxol

Keywords: Baccatin III; Heck-Reaktionen; Taxol; Totalsynthesen