201993-93-3

Upstream product

• 201993-91-1 (1R,3R,4R)-4-Benzyloxymethoxy-3-methoxy-cyclohexanecarboxylic acid isopropyl ester 
• 3587-60-8 Benzyloxymethyl chloride 
• 116498-92-1 (1R,4R,5R)-4-hydroxy-6-oxabicyclo[3.2.1]octan-7-one 
• 201993-84-2 Trifluoro-acetic acid (1R,4R,5R)-7-oxo-6-oxa-bicyclo[3.2.1]oct-4-yl ester 
• 201993-87-5 (1R,4R,5R)-4-Benzyloxymethoxy-6-oxa-bicyclo[3.2.1]octan-7-one 

Downstream Products

• 201994-08-3 (S)-4-Benzyl-3-[(E)-(2S,3S)-5-((1R,3R,4R)-4-benzyloxymethoxy-3-methoxy-cyclohexyl)-3-hydroxy-2,4-dimethyl-pent-4-enoyl]-oxazolidin-2-one 
• 201994-14-1 (E)-(2S,3S)-5-((1R,3R,4R)-4-Benzyloxymethoxy-3-methoxy-cyclohexyl)-3-(tert-butyl-dimethyl-silanyloxy)-2,4-dimethyl-pent-4-enoic acid methoxy-methyl-amide 
• 201994-11-8 (E)-(2S,3S)-5-((1R,3R,4R)-4-Benzyloxymethoxy-3-methoxy-cyclohexyl)-3-hydroxy-2,4-dimethyl-pent-4-enoic acid methoxy-methyl-amide 
• 201994-16-3 (E)-(2S,3S)-5-((1R,3R,4R)-4-Benzyloxymethoxy-3-methoxy-cyclohexyl)-3-(tert-butyl-dimethyl-silanyloxy)-2,4-dimethyl-pent-4-enal 
• 201994-38-9 (E)-3-((1R,3R,4R)-4-Benzyloxymethoxy-3-methoxy-cyclohexyl)-2-methyl-propenal 

Relevant academic research and scientific papers

Synthetic studies on the immunosuppressive agent FK-506: Enantioselective synthesis of a C22-C34 fragment

The C28-C32 cyclohexyl group of the natural product, FK-506, was prepared enantioselectively from the iodolactone by replacement of iodide with retention of configuration. The C27-C28 trisubstituted olefin was introduced stereoselectively via a classical aldol/elimination sequence employing titanium enolate methodology. Elaboration of this chemistry has led to a synthesis of a C22-C34 fragment of the natural product.