148933-60-2

Upstream product

• 58479-61-1 tert-butylchlorodiphenylsilane 
• 168777-79-5 (2R,3R,4R,5R)-1,6-Bis-(tert-butyl-diphenyl-silanyloxy)-2,5-dimethoxy-hexane-3,4-diol 

Downstream Products

• 148933-61-3 (4R,5S)-3-{(2R,4S)-2-[(1R,2R)-3-(tert-Butyl-diphenyl-silanyloxy)-1-hydroxy-2-methoxy-propyl]-4-methyl-hex-5-enoyl}-4-methyl-5-phenyl-oxazolidin-2-one 
• 148933-78-2 Toluene-4-sulfonic acid (2S,4S)-2-[(1R,2R)-3-(tert-butyl-diphenyl-silanyloxy)-1-hydroxy-2-methoxy-propyl]-4-methyl-hex-5-enyl ester 
• 148933-77-1 (2S,3R,4R)-5-(tert-Butyl-diphenyl-silanyloxy)-4-methoxy-2-((S)-2-methyl-but-3-enyl)-pentane-1,3-diol 
• 148933-62-4 (2R,3R,4R,6S)-1-(tert-Butyl-diphenyl-silanyloxy)-2-methoxy-4,6-dimethyl-oct-7-en-3-ol 
• 477351-68-1 C₅₆H₈₆N₆O₁₃Si 
• 477351-80-7 (2S,3aR,5S,6S,7aS)-1-{(R)-2-[(R)-3-(tert-Butyl-diphenyl-silanyloxy)-2-methoxy-propionylamino]-4-methyl-pentanoyl}-5,6-bis-methoxymethoxy-octahydro-indole-2-carboxylic acid 
• 477351-67-0 (2S,3aR,5S,6S,7aS)-1-{(R)-2-[(R)-3-(tert-Butyl-diphenyl-silanyloxy)-2-methoxy-propionylamino]-4-methyl-pentanoyl}-5,6-bis-methoxymethoxy-octahydro-indole-2-carboxylic acid methyl ester 
• 477351-75-0 (R)-2-[(R)-3-(tert-Butyl-diphenyl-silanyloxy)-2-methoxy-propionylamino]-4-methyl-pentanoic acid benzyl ester 
• 477351-66-9 (R)-2-[(R)-3-(tert-Butyl-diphenyl-silanyloxy)-2-methoxy-propionylamino]-4-methyl-pentanoic acid 
• 477351-74-9 (R)-3-(tert-butyldiphenylsilyloxy)-2-methoxypropionic acid 

Relevant academic research and scientific papers

Total synthesis and structural confirmation of the marine natural product dysinosin A: A novel inhibitor of thrombin and Factor VIIa

The structure and absolute configuration of the marine antithrombotic product dysinosin A was confirmed by total synthesis. The strategy involved disconnections to three subunits, of which two were synthesized from the readily available l-glutamic acid, d

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