148933-90-8

Basic information

• Product Name: C₈₁H₁₂₅NO₁₂Si₂
• Synonyms: C₈₁H₁₂₅NO₁₂Si₂
• CAS NO: 148933-90-8
• Molecular Weight: 1361.05
• Mol File: 148933-90-8.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: C₈₁H₁₂₅NO₁₂Si₂(CAS DataBase Reference)
• NIST Chemistry Reference: C₈₁H₁₂₅NO₁₂Si₂(148933-90-8)
• EPA Substance Registry System: C₈₁H₁₂₅NO₁₂Si₂(148933-90-8)

Safety Data

• Hazardous Substances Data: 148933-90-8(Hazardous Substances Data)

Upstream product

• 148933-70-4 2-[(1R,4R,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-methoxy-cyclohex-2-enyl]-N,N-dimethyl-acetamide 
• 148933-84-0 2-[(1S,4R,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-methoxy-cyclohex-2-enyl]-ethanol 
• 168777-83-1 (1S,5R,6R)-6-(tert-Butyl-dimethyl-silanyloxy)-5-methoxy-cyclohex-2-enol 
• 168777-84-2 2-[(1S,3R,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-3-methoxy-cyclohexyl]-ethanol 
• 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 
• 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 
• 168777-85-3 (4R,5S)-3-{(E)-3-[(1R,3R,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-3-methoxy-cyclohexyl]-acryloyl}-4-methyl-5-phenyl-oxazolidin-2-one 
• 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 
• 148933-74-8 C₈₀H₁₁₅NO₁₂Si₂ 
• 168777-87-5 C₇₇H₁₁₄O₁₂SSi₂ 

Downstream Products

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

Relevant articles and documents

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