126789-40-0

Upstream product

• 126821-31-6 (S)-4-Benzyl-3-[(2S,3R,4R,6S,7R,8S,10R)-7-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-6,8-dimethoxy-2-(4-methoxy-benzyloxy)-4,10-dimethyl-11-triisopropylsilanyloxy-undecanoyl]-oxazolidin-2-one 
• 126788-95-2 [(2R,5R,6S,8R)-9-Benzyloxy-4,6-dimethoxy-5-(4-methoxy-benzyloxy)-2,8-dimethyl-nonyloxy]-tert-butyl-dimethyl-silane 
• 126789-01-3 2,2-Dimethyl-propionic acid (2R,4S,5R,6S,8R)-5-(tert-butyl-dimethyl-silanyloxy)-8-[1,3]dithian-2-yl-4,6-dimethoxy-2-methyl-nonyl ester 
• 126788-98-5 2,2-Dimethyl-propionic acid (2R,4S,5R,6S,8R)-5,9-bis-(tert-butyl-dimethyl-silanyloxy)-4,6-dimethoxy-2,8-dimethyl-nonyl ester 
• 126789-06-8 2-[(1R,3S,4R,5S,7R)-4-(tert-Butyl-dimethyl-silanyloxy)-3,5-dimethoxy-1,7-dimethyl-8-triisopropylsilanyloxy-octyl]-[1,3]dithiane 
• 126789-10-4 (2R,4S,5R,6S,8R)-5-(tert-Butyl-dimethyl-silanyloxy)-4,6-dimethoxy-2,8-dimethyl-9-triisopropylsilanyloxy-nonanal 
• 126788-99-6 2,2-Dimethyl-propionic acid (2R,4S,5R,6S,8R)-5-(tert-butyl-dimethyl-silanyloxy)-4,6-dimethoxy-2,8-dimethyl-9-oxo-nonyl ester 
• 126789-09-1 (2R,4S,5R,6S,8R)-5-(tert-Butyl-dimethyl-silanyloxy)-1,1,4,6-tetramethoxy-2,8-dimethyl-9-triisopropylsilanyloxy-nonane 
• 126789-00-2 2,2-Dimethyl-propionic acid (2R,4S,5R,6S,8R)-8-[1,3]dithian-2-yl-5-hydroxy-4,6-dimethoxy-2-methyl-nonyl ester 
• 118949-45-4 (2R,4S,5S,6S,8R)-2,8-Dimethyl-4,6-dimethoxy-5-t-butyldimethylsilyloxy-9-pivaloyloxynonanol 
• 126788-97-4 (2R,4S,5R,6S,8R)-1-Pivaloyloxy-2,8-dimethyl-4,6-dimethoxy-5-hydroxyl-9-t-butyldimethylsilyloxynonane 
• 118949-46-5 (2R,4S,5R,6S,8R)-5-(tert-Butyl-dimethyl-silanyloxy)-8-[1,3]dithian-2-yl-4,6-dimethoxy-2-methyl-nonan-1-ol 
• 126788-96-3 (2R,4S,5R,8R)-9-(tert-Butyl-dimethyl-silanyloxy)-4,6-dimethoxy-2,8-dimethyl-nonane-1,5-diol 
• 69739-34-0 t-butyldimethylsiyl triflate 

Downstream Products

• 126789-41-1 (S)-1-[(2S,3R,4R,6S,7R,8S,10R)-7-(tert-Butyl-dimethyl-silanyloxy)-6,8-dimethoxy-2-(4-methoxy-benzyloxy)-4,10-dimethyl-3-triethylsilanyloxy-11-triisopropylsilanyloxy-undecanoyl]-piperidine-2-carboxylic acid tert-butyl ester 

Relevant academic research and scientific papers

Process for synthesis of FK-506 and tricarbonyl intermediates

A process is described for the total synthesis of the macrolide immunosuppressant, FK-506, and important tricarbonyl process intermediates thereof. The tricarbonyl intermediates can be produced by the mild oxidation of 2,3-dihydroxy carboxylate compounds containing olefin moieties.

Chemistry of tricarbonyl hemiketals and application of Evans' technology to the total synthesis of the immunosuppressant (-)-FK-506

Details of model studies probing the chemistry of the tricarbonyl region of FK-506 are presented, and their use in designing a successful route to this immunosuppressant is outlined. Application of asymmetric oxazolidinone alkylation/aldol methodology to a convergent, highly flexible synthesis of the C10-C18 fragment and to improvements in the preparation of the C20-C34 segment are also discussed.