164592-91-0

Upstream product

• 79271-56-0 triethylsilyl trifluoromethyl sulfonate 
• 186417-28-7 C₆₆H₁₁₃NO₁₃Si₂ 
• 101977-00-8 (2R,3R,7S,10R)-7-Allyl-2,3,10-trimethyl-1,4,6-trioxa-spiro[4.5]decane 
• 186449-08-1 C₅₉H₁₀₈O₈S₄Si₂ 
• 164592-79-4 C₅₇H₁₀₂O₇S₄Si₂ 
• 164592-81-8 C₅₈H₁₀₂O₆S₄Si₂ 
• 164592-83-0 C₅₀H₉₄O₅S₄Si₂ 
• 164592-72-7 (S)-1-[(E)-(4R,7S,9S)-7-(tert-Butyl-dimethyl-silanyloxy)-9-methoxy-4,10-dimethyl-2,3-dioxo-13-trimethylsilanyl-tridec-10-en-12-ynoyl]-piperidine-2-carboxylic acid methyl ester 
• 186417-44-7 (S)-1-[(Z)-(4R,7S,9S)-7-(tert-Butyl-dimethyl-silanyloxy)-9-methoxy-4,10-dimethyl-2,3-dioxo-13-trimethylsilanyl-tridec-10-en-12-ynoyl]-piperidine-2-carboxylic acid methyl ester 
• 186417-37-8 (S)-1-[(E)-(4R,7S,9S)-7-(tert-Butyl-dimethyl-silanyloxy)-3-hydroxy-9-methoxy-4,10-dimethyl-13-trimethylsilanyl-tridec-10-en-12-ynoyl]-piperidine-2-carboxylic acid methyl ester 
• 186417-43-6 (S)-1-[(Z)-(4R,7S,9S)-7-(tert-Butyl-dimethyl-silanyloxy)-3-hydroxy-9-methoxy-4,10-dimethyl-13-trimethylsilanyl-tridec-10-en-12-ynoyl]-piperidine-2-carboxylic acid methyl ester 
• 186417-42-5 (S)-1-[(Z)-(4R,7S,9S)-7-(tert-Butyl-dimethyl-silanyloxy)-3-hydroxy-9-methoxy-4,10-dimethyl-13-trimethylsilanyl-tridec-10-en-12-ynoyl]-piperidine-2-carboxylic acid 
• 186417-46-9 (S)-1-{2-[(2S,3R,6S)-6-((Z)-(S)-2-Methoxy-3-methyl-hex-3-en-5-ynyl)-3-methyl-2-triethylsilanyloxy-tetrahydro-pyran-2-yl]-2-oxo-acetyl}-piperidine-2-carboxylic acid methyl ester 
• 186417-35-6 (E)-(2R,5S,7S)-5-(tert-Butyl-dimethyl-silanyloxy)-7-methoxy-2,8-dimethyl-11-trimethylsilanyl-undec-8-en-10-ynoic acid (1R,2R)-2-(tert-butyl-dimethyl-silanyloxy)-1-methyl-propyl ester 

Downstream Products

• 186417-28-7 C₆₆H₁₁₃NO₁₃Si₂ 
• 186417-29-8 C₇₂H₁₂₇NO₁₃Si₃ 
• 53123-88-9 sirolimus 

Relevant academic research and scientific papers

A unified total synthesis of the immunomodulators (-)-rapamycin and (-)-27-demethoxyrapamycin: Assembly of the common C(1-20) perimeter and final elaboration

The potent, naturally occurring immunomodulators (-)-rapamycin (1) and (-)-27-demethoxyrapamycin (2) have been synthesized via a unified and highly convergent strategy. In the preceding paper we discussed the construction of common building blocks A-C and their linkage to provide the C(21-42) segments of 1 and 2. Herein we describe model studies of triene generation and hydroxyl deprotection, the preparation and coupling of building blocks D and E, a two-step protocol for macrocycle formation via union of the ABC and DE subtargets, and completion of the total syntheses. The synthesis of 27-demethoxyrapamycin (2) confirmed the assigned structure.