148933-75-9

Upstream product

• 168777-87-5 C₇₇H₁₁₄O₁₂SSi₂ 
• 69274-86-8 (S)-(+)-4-methylhex-5-enoic acid 
• 168777-81-9 (3S,4R)-1-[(tert-butyldimethylsilyl)oxy]-4-methylhex-5-en-3-ol 
• 128209-97-2 (1R,3R,4R)-4-[(tert-butyldimethylsilyl)oxy]-3-methoxycyclohexane-1-carbaldehyde 
• 148933-79-3 (2R,3R,4R,6S)-2-Methoxy-4,6-dimethyl-oct-7-ene-1,3-diol 
• 148933-83-9 (1R,2R,3R)-2-(tert-Butyl-dimethyl-silanyloxy)-3-methoxy-cyclohexanol 
• 148933-68-0 (5R,6S)-6-(tert-Butyl-dimethyl-silanyloxy)-5-methoxy-cyclohex-2-enone 
• 148933-67-9 (2S,3R)-2-(tert-Butyl-dimethyl-silanyloxy)-3-methoxy-cyclohexanone 
• 148933-66-8 ((1S,2R,6R)-2-Benzyloxy-6-methoxy-cyclohexyloxy)-tert-butyl-dimethyl-silane 
• 148933-80-6 (2R,3R,4R,6S)-2-Methoxy-3-(4-methoxy-benzyloxy)-4,6-dimethyl-oct-7-en-1-ol 
• 148933-64-6 tert-Butyl-[(3S,4R)-3-(4-methoxy-benzyloxy)-4-methyl-hex-5-enyloxy]-dimethyl-silane 
• 148933-56-6 (2S,3R,4R,6S)-2-Methoxy-3-(4-methoxy-benzyloxy)-4,6-dimethyl-oct-7-enal 
• 148933-81-7 (2S,3S)-5-(tert-Butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-2-methyl-pentanal 
• 148933-59-9 (4R,5S)-4-Methyl-3-((S)-4-methyl-hex-5-enoyl)-5-phenyl-oxazolidin-2-one 

Downstream Products

• 148933-55-5 C₇₂H₁₂₈INO₈Si₄ 
• 148933-91-9 C₈₀H₁₂₃NO₁₃Si₂ 
• 148933-76-0 C₈₁H₁₂₄INO₁₂Si₂ 
• 168777-88-6 C₆₅H₁₀₈INO₁₀Si₂ 
• 148933-90-8 C₈₁H₁₂₅NO₁₂Si₂ 

Relevant academic research and scientific papers

Total Synthesis of Rapamycin

Details of the total synthesis of rapamycin (1) are reported.The synthesis required the preparation of intermediates 4-9 in nonracemic form; key coupling reactions included a chromium-mediated addition of vinyl iodide 8 to aldehyde 7 and an Evans aldol reaction to couple fragments 62 and 9.Intermediates 4 and 6 were joined through an amide bond formation to afford advanced intermediate 71.Swern oxidation of the diol in 71 was followed by a selective removal of the TES groups and a second Swern oxidation.Finally, removal of the remaining silyl protecting groups provided fully deprotected, penultimate intermediate 2 in which all carbons were in their proper oxidation state.Macrocyclization was achived through a tandem inter/intramolecular palladium-mediated Stille coupling reaction between distannylethene 3 and bis(vinyl iodide) 2.This latter process accomplished in one step the installation of the remaining two carbons of the natural product and the completion of its total synthesis. - Keywords: rapamycin, stannylethenes, Stille coupling, vinyl iodides