226079-75-0

Upstream product

• 59276-33-4 veratraldehyde dimethyl acetal 
• 214060-16-9 (3R,4S,5R)-6-(tert-butyldiphenylsilyloxy)-4-hydroxy-3-hydroxymethyl-5-methyl-1-hexene 
• 214060-14-7 (2S,3S,4R)-5-(tert-butyldiphenylsilyloxy)-2,3-epoxy-4-methylpentan-1-ol 
• 226079-73-8 methyl (2E,4S)-5-(tert-butyldiphenylsilyloxy)-4-methyl-2-pentenoate 
• 58479-61-1 tert-butylchlorodiphenylsilane 
• 95514-04-8 (S)-3-(tert-butyldiphenylsilyloxy)-2-methylpropan-1-ol 
• 91751-24-5 (R)-3-[(tert-butyldiphenylsilyl)oxy]-2-methylpropanal 
• 127665-68-3 (4S)-5-(tert-butyldiphenylsilyloxy)-4-methyl-2-penten-1-ol 

Downstream Products

• 214060-10-3 (2S,3S,4R,5S,6R)-7-(tert-butyldiphenylsilyloxy)-3,5-<(S)-3,4-dimethoxybenzylidenedioxy>-2-methoxymethoxy-4,6-dimethyl-1-heptyl 2,2-dimethylpropanoate 
• 226080-03-1 (E)-(3S,6R,7S)-7-[(2S,4S,5R,6S)-2-(3,4-Dimethoxy-phenyl)-6-((S)-1-methoxymethoxy-2-triethylsilanyloxy-ethyl)-5-methyl-[1,3]dioxan-4-yl]-6-methoxymethoxy-3,5-dimethyl-oct-4-en-2-ol 
• 226079-49-8 (3S,4E,6R,7S,8S,9R,10S,11S)-12-triethylsilyloxy-8,10-<(S)-3,4-dimethoxybenzylidenedioxy>-6,11-bis(methoxymethoxy)-3,5,7,9-tetramethyl-4-dodecen-2-one 
• 226079-92-1 (2R,3S,4R,5S,6R)-2,3-Diacetoxy-7-(tert-butyl-diphenyl-silanyloxy)-5-(3,4-dimethoxy-benzyloxy)-4,6-dimethyl-heptanoic acid methyl ester 
• 226079-68-1 (2S,3S,4R,5S,6S,7R,8E,10S)-11-hydroxy-3,5-<(S)-3,4-dimethoxybenzylidenedioxy>-2,7-bis(methoxymethoxy)-4,6,8,10-tetramethyl-8-undecen-1-yl 2,2-dimethylpropanoate 
• 226079-81-8 methyl (2R,3S,4R,5S,6R)-7-(tert-butyldiphenylsilyloxy)-3,5-<(S)-3,4-dimethoxybenzylidenedioxy>-2-methoxymethoxy-4,6-dimethylheptanoate 
• 226079-82-9 (S)-2-[(2S,4S,5R,6S)-6-[(R)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-2-(3,4-dimethoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-2-methoxymethoxy-ethanol 
• 214060-21-6 methyl (2S,3R,4R,5S,6R)-7-(tert-butyldiphenylsilyloxy)-2,3-dihydroxy-5-(3,4-dimethoxybenzyloxy)-4,6-dimethylheptanoate 
• 226080-00-8 2,2-Dimethyl-propionic acid (S)-2-[(2S,4S,5R,6S)-2-(3,4-dimethoxy-phenyl)-6-((E)-(1S,2R,5S)-2-methoxymethoxy-1,3,5-trimethyl-6-oxo-hex-3-enyl)-5-methyl-[1,3]dioxan-4-yl]-2-methoxymethoxy-ethyl ester 
• 226079-53-4 methyl (2R,3S,4R,5S,6R)-7-(tert-butyldiphenylsilyloxy)-2-hydroxy-3,5-<(S)-3,4-dimethoxybenzylidenedioxy>-4,6-dimethylheptanoate 
• 226079-54-5 methyl (2S,3R,4R,5S,6R)-7-(tert-butyldiphenylsilyloxy)-2-hydroxy-3,5-<(S)-3,4-dimethoxybenzylidenedioxy>-4,6-dimethylheptanoate 
• 226080-01-9 (2S,3S,4R,5S,6S,7R,8E,10S,11RS)-3,5-<(S)-3,4-dimethoxybenzylidenedioxy>-2,7-bis(methoxymethoxy)-4,6,8,10-tetramethyl-8-dodecene-1,11-diol 
• 226079-94-3 (2R,3S,4R,5S,6R)-2,3-Diacetoxy-7-(tert-butyl-diphenyl-silanyloxy)-5-methoxymethoxy-4,6-dimethyl-heptanoic acid methyl ester 
• 226080-06-4 tert-Butyl-{(R)-2-[(2R,4S,5S,6R)-2-(3,4-dimethoxy-phenyl)-5-methyl-6-vinyl-[1,3]dioxan-4-yl]-propoxy}-diphenyl-silane 

Relevant academic research and scientific papers

Synthetic studies of the 18-membered antitumor macrolide, tedanolide. 3. Stereocontrolled synthesis of the C1-C12 part via a synthesis of the C1-C7 fragment by a mismatched but efficient sharpless dihydroxylation and its coupling with the C8-C11 fragment

The C1-C12 part (4) of tedanolide (1) was synthesized starting from methyl (R)-3-hydroxy-2-methylpropionate (11a) via a coupling between the C1- C7 aldehyde (6) and the C8-C11 iodoalkene (7a). For a synthesis of 6, a mismatched but highly efficient Sharpless dihydroxylation of the α,β- unsaturated ester (15) with AD-mix-α was successfully applied. Compound 7a was synthesized using hydrozirconation to the alkyne (32).

Synthetic studies of 18-membered antitumor macrolide, tedanolide. 2. Stereoselective synthesis of the C1 - C7 fragment via a mismatched but highly efficient sharpless dihydroxylation

The C1 - C7 fragment (4) of tedanolide (1) was synthesized starting from methyl (R)-3-hydroxy-2-methyl-propionate via a mismatched but highly efficient sharpless dihydroxylation of the C1 - C7 α,β-unsaturated ester (6) with AD-mix-α.