226079-93-2

Upstream product

• 127665-68-3 (4S)-5-(tert-butyldiphenylsilyloxy)-4-methyl-2-penten-1-ol 
• 214060-19-2 methyl (2R,3S,4R,5S,6R)-7-(tert-butyldiphenylsilyloxy)-2,3-dihydroxy-5-(3,4-dimethoxybenzyloxy)-4,6-dimethylheptanoate 
• 214060-11-4 methyl (2E,4S,5R,6R)-7-(tert-butyldiphenylsilyloxy)-5-(3,4-dimethoxybenzyloxy)-4,6-dimethyl-2-heptenoate 
• 226079-78-3 (3S,4S,5R)-6-(tert-Butyl-diphenyl-silanyloxy)-4-(3,4-dimethoxy-benzyloxy)-3,5-dimethyl-hexane-1,2-diol 
• 214060-17-0 (3R,4S,5R)-6-(tert-butyldiphenylsilyloxy)-3-hydroxymethyl-4-(3,4-dimethoxybenzyloxy)-5-methyl-1-hexene 
• 226079-75-0 tert-Butyl-{(R)-2-[(4S,5R)-2-(3,4-dimethoxy-phenyl)-5-vinyl-[1,3]dioxan-4-yl]-propoxy}-diphenyl-silane 
• 226079-52-3 (3S,4R,5R)-6-(tert-butyldiphenylsilyloxy)-4-(3,4-dimethoxybenzyloxy)-3,5-dimethyl-1-hexene 
• 226079-79-4 (2R,3S,4R)-5-(tert-Butyl-diphenyl-silanyloxy)-3-(3,4-dimethoxy-benzyloxy)-2,4-dimethyl-pentanal 
• 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 
• 95514-03-7 (R)-methyl 3-(tert-butyl(diphenyl)silyloxy)-2-methylpropanoate 
• 95514-04-8 (S)-3-(tert-butyldiphenylsilyloxy)-2-methylpropan-1-ol 

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).