126789-43-3

Upstream product

• 80522-42-5 triisopropylsilyl trifluoromethanesulfonate 
• 127492-57-3 (1E,9E)-(3S,4R,5S,7R,8R,12S,14S,15R,16S,18R)-8-Allyl-7,15-bis-(tert-butyl-dimethyl-silanyloxy)-18-[1,3]dithian-2-yl-14,16-dimethoxy-1-((1R,3R,4R)-3-methoxy-4-triisopropylsilanyloxy-cyclohexyl)-2,4,10,12-tetramethyl-nonadeca-1,9-diene-3,5-diol 
• 118977-91-6 C₇₅H₁₅₂O₈S₂Si₅ 
• 69739-34-0 t-butyldimethylsiyl triflate 
• 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 
• 126788-97-4 (2R,4S,5R,6S,8R)-1-Pivaloyloxy-2,8-dimethyl-4,6-dimethoxy-5-hydroxyl-9-t-butyldimethylsilyloxynonane 
• 118949-45-4 (2R,4S,5S,6S,8R)-2,8-Dimethyl-4,6-dimethoxy-5-t-butyldimethylsilyloxy-9-pivaloyloxynonanol 
• 127492-56-2 C₆₈H₁₂₄O₉S₂Si₃ 
• 126788-96-3 (2R,4S,5R,8R)-9-(tert-Butyl-dimethyl-silanyloxy)-4,6-dimethoxy-2,8-dimethyl-nonane-1,5-diol 
• 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 
• 126788-99-6 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 
• 126789-00-2 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 
• 127492-55-1 C₇₆H₁₂₉F₃O₁₃S₃Si₃ 

Downstream Products

• 126789-44-4 C₈₀H₁₅₅NO₁₁S₂Si₄ 
• 127517-03-7 C₆₆H₁₃₂O₉Si₄ 

Relevant academic research and scientific papers

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.

A Formal Synthesis of FK-506. Exploration of Some Alternatives to Macrolactamization

The coupling of the previously described subunits 2, 3, and 4 is described.The C28-C27 E-double bond is fashioned from a sulfurane induced dehydration of alcohol 11.The C19-C20 E-double bond was constructed via a modified Julia process culminating in a reductive elimination of a vicinal trifluoroacetoxy sulfone (see 22 -> 23 -> 24 and 25).The synthesis of intermediates anticipating potential macrolactonization are also described.