148933-81-7

Upstream product

• 1015421-58-5 PMBTCA 
• 1082395-53-6 C₂₁H₃₄O₅Si 
• 1082395-57-0 C₂₂H₄₀O₅Si 
• 89922-82-7 3-(tert-butyldimethylsilanyloxy)propionaldehyde 
• 168777-81-9 (3S,4R)-1-[(tert-butyldimethylsilyl)oxy]-4-methylhex-5-en-3-ol 
• 56599-24-7 p-methoxybenzyl trichloroacetate 
• 148933-64-6 tert-Butyl-[(3S,4R)-3-(4-methoxy-benzyloxy)-4-methyl-hex-5-enyloxy]-dimethyl-silane 

Downstream Products

• 148933-82-8 tert-Butyl-[(3S,4R)-6,6-dibromo-3-(4-methoxy-benzyloxy)-4-methyl-hex-5-enyloxy]-dimethyl-silane 
• 1520158-82-0 C₂₆H₄₀O₈ 
• 1520158-41-1 C₃₈H₇₀O₉Si₂ 
• 168960-76-7 (E)-(3S,4R,7S,8R,9R,10R,12S)-1-(tert-Butyl-dimethyl-silanyloxy)-8-methoxy-3,9-bis-(4-methoxy-benzyloxy)-4,6,10,12-tetramethyl-tetradeca-5,13-dien-7-ol 
• 168777-88-6 C₆₅H₁₀₈INO₁₀Si₂ 
• 148933-76-0 C₈₁H₁₂₄INO₁₂Si₂ 
• 148933-74-8 C₈₀H₁₁₅NO₁₂Si₂ 
• 148933-91-9 C₈₀H₁₂₃NO₁₃Si₂ 
• 148933-90-8 C₈₁H₁₂₅NO₁₂Si₂ 
• 168777-87-5 C₇₇H₁₁₄O₁₂SSi₂ 
• 148933-55-5 C₇₂H₁₂₈INO₈Si₄ 
• 168777-86-4 (E)-(2S,3S,5S,6R,9R,10S,11R,12R,14S)-2-[(1S,3R,4R)-4-(tert-Butyl-diphenyl-silanyloxy)-3-methoxy-cyclohexylmethyl]-10-methoxy-5,11-bis-(4-methoxy-benzyloxy)-6,8,12,14-tetramethyl-9-triisopropylsilanyloxy-hexadeca-7,15-diene-1,3-diol 
• 148933-75-9 (E)-(2R,3S,5S,6R,9R,10S,11R,12R,14S)-1-[(1S,3R,4R)-4-(tert-Butyl-diphenyl-silanyloxy)-3-methoxy-cyclohexyl]-10-methoxy-5,11-bis-(4-methoxy-benzyloxy)-2,6,8,12,14-pentamethyl-9-triisopropylsilanyloxy-hexadeca-7,15-dien-3-ol 
• 148933-86-2 C₅₀H₈₆O₇Si₂ 

Relevant academic research and scientific papers

Total synthesis of (-)-dictyostatin, a microtubule-stabilising anticancer macrolide of marine sponge origin

An efficient convergent synthesis of the anticancer marine macrolide (-)-dictyostatin is described that proceeds in 4.6% yield over 27 steps. Most of the stereocentres were configured using substrate control, making use of a common building block to insta

Total synthesis of a potent hybrid of the anticancer natural products dictyostatin and discodermolide

A potent dictyostatin-discodermolide hybrid was designed and synthesised; it showed enhanced cell growth inhibitory activity relative to discodermolide in four human cancer cell lines including the Taxol-resistant NCI/ADR-Res cell line. The Royal Society of Chemistry.

Synthesis and biological evaluation of novel analogues of dictyostatin

Novel analogues of the microtubule-stabilising agent dictyostatin were designed using existing SAR information from the structurally related discodermolide, synthesised by a late-stage diversification strategy and evaluated in vitro for growth inhibition

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