116386-65-3

Upstream product

• 116386-61-9 (1R,3R,4R)-3-Methoxy-4-triisopropylsilanyloxy-cyclohexanecarbaldehyde 
• 126788-79-2 (S)-4-Benzyl-3-[(E)-3-hydroxy-5-(3-methoxy-4-triisopropylsilanyloxy-cyclohexyl)-2,4-dimethyl-pent-4-enoyl]-oxazolidin-2-one 
• 126788-80-5 (E)-(2S,3S)-3-Hydroxy-5-((1R,3R,4R)-3-methoxy-4-triisopropylsilanyloxy-cyclohexyl)-2,4-dimethyl-pent-4-enoic acid methoxy-methyl-amide 
• 126788-77-0 (1R,3R,4R)-3-Methoxy-4-triisopropylsilanyloxy-cyclohexanecarboxylic acid methoxy-methyl-amide 
• 116386-60-8 (1R,3R,4R)-3-Hydroxy-4-triisopropylsilanyloxy-cyclohexanecarboxylic acid methoxy-methyl-amide 
• 116386-63-1 (E)-3-((1R,3R,4R)-3-Methoxy-4-triisopropylsilanyloxy-cyclohexyl)-2-methyl-propenal 
• 126788-76-9 (1R,4R,5R)-4-Triisopropylsilanyloxy-6-oxa-bicyclo[3.2.1]octan-7-one 
• 52892-14-5 (1S,3R)-7-Oxa-bicyclo[4.1.0]heptane-3-carboxylic acid 
• 88255-83-8 3,4-Dihydroxycyclohexanecarboxylic acid-γ-lactone 
• 4771-80-6 1,2,5,6-tetrahydrobenzoic acid 
• 116409-60-0 Imidazole-1-carbothioic acid O-((1R,2S,6R,8R)-9-oxo-4-thioxo-3,5,10-trioxa-tricyclo[6.2.1.0^2,6]undec-8-yl) ester 
• 127126-09-4 (1R,3R,4R)-3-Methoxy-4-triisopropylsilanyloxy-cyclohexanecarboxylic acid methoxy-methyl-amide 
• 116386-60-8 (1R,3R,4R)-3-Hydroxy-4-triisopropylsilanyloxy-cyclohexanecarboxylic acid methoxy-methyl-amide 
• 116386-63-1 (E)-2-Methyl-3-<(1R,3R,4R)-3-methoxy-4-<(triisopropylsilyl)oxy>cyclohexyl>-2-propenal 

Downstream Products

• 126788-82-7 (S)-4-Benzyl-3-[(E)-(2S,3R,4R,5S)-2-chloro-3-hydroxy-7-((1R,3R,4R)-3-methoxy-4-triisopropylsilanyloxy-cyclohexyl)-4,6-dimethyl-5-triethylsilanyloxy-hept-6-enoyl]-oxazolidin-2-one 
• 116386-67-5 (E)-(3S,4R,5S)-7-((1R,3R,4R)-3-Methoxy-4-triisopropylsilanyloxy-cyclohexyl)-4,6-dimethyl-5-triethylsilanyloxy-3-triisopropylsilanyloxy-hept-6-enal 
• 126788-84-9 (E)-(3S,4R,5S)-3-Hydroxy-7-((1R,3R,4R)-3-methoxy-4-triisopropylsilanyloxy-cyclohexyl)-4,6-dimethyl-5-triethylsilanyloxy-hept-6-enoic acid methoxy-methyl-amide 
• 126788-85-0 (E)-(3S,4R,5S)-7-((1R,3R,4R)-3-Methoxy-4-triisopropylsilanyloxy-cyclohexyl)-4,6-dimethyl-5-triethylsilanyloxy-3-triisopropylsilanyloxy-hept-6-enoic acid methoxy-methyl-amide 
• 126788-83-8 (S)-4-Benzyl-3-[(E)-(3S,4R,5S)-3-hydroxy-7-((1R,3R,4R)-3-methoxy-4-triisopropylsilanyloxy-cyclohexyl)-4,6-dimethyl-5-triethylsilanyloxy-hept-6-enoyl]-oxazolidin-2-one 
• 116386-66-4 (E)-(3S,4R,5S)-3-Hydroxy-7-((1R,3R,4R)-3-methoxy-4-triisopropylsilanyloxy-cyclohexyl)-4,6-dimethyl-5-triethylsilanyloxy-hept-6-enoic acid (S)-2-hydroxy-1,2,2-triphenyl-ethyl ester 

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.

DIASTEREOSPECIFIC, NON-RACEMIC SYNTHESIS OF THE C.20-C.34 SEGMENT OF THE NOVEL IMMUNOSUPPRESSANT FK-506

An efficient stereocontrolled route to construct the C.20-C.34 moiety of FK-506 is described.