368878-72-2

Upstream product

• 314021-43-7 {5-[6-(2-benzenesulfonyl-ethyl)-6-methoxy-3,6-dihydro-2H-pyran-2-yl]-pent-4-enyloxy}-tert-butyl-diphenyl-silane 
• 368878-71-1 (S)-3-((2S,3S,5R)-5-Methoxy-3-triethylsilanyloxy-tetrahydro-furan-2-yl)-2-methyl-propionaldehyde 
• 368878-69-7 (S)-3-((2S,3S,5R)-5-Methoxy-3-triethylsilanyloxy-tetrahydro-furan-2-yl)-2-methyl-propionic acid methyl ester 
• 368878-79-9 (S)-3-((2S,3S,5R)-5-Methoxy-3-triethylsilanyloxy-tetrahydro-furan-2-yl)-2-methyl-propan-1-ol 
• 314021-38-0 (S)-3-((2S,3S,5R)-3-Hydroxy-5-methoxy-tetrahydro-furan-2-yl)-2-methyl-propionic acid methyl ester 
• 79271-56-0 triethylsilyl trifluoromethyl sulfonate 

Downstream Products

• 368878-75-5 (2S,4S)-2-Benzenesulfonyl-1-{(2S,6S)-6-[(E)-5-(tert-butyl-diphenyl-silanyloxy)-pent-1-enyl]-2-methoxy-5,6-dihydro-2H-pyran-2-yl}-5-((2S,3S,5R)-3-hydroxy-5-methoxy-tetrahydro-furan-2-yl)-4-methyl-pentan-3-one 
• 368878-80-2 (2R,4S)-2-Benzenesulfonyl-1-{(2S,6S)-6-[(E)-5-(tert-butyl-diphenyl-silanyloxy)-pent-1-enyl]-2-methoxy-5,6-dihydro-2H-pyran-2-yl}-5-((2S,3S,5R)-3-hydroxy-5-methoxy-tetrahydro-furan-2-yl)-4-methyl-pentan-3-one 
• 368878-73-3 (S)-5-{(2S,6S)-6-[(E)-5-(tert-Butyl-diphenyl-silanyloxy)-pent-1-enyl]-2-methoxy-5,6-dihydro-2H-pyran-2-yl}-1-((2S,3S,5R)-5-methoxy-3-triethylsilanyloxy-tetrahydro-furan-2-yl)-2-methyl-pentan-3-one 
• 368878-70-0 (S)-2-Benzenesulfonyl-1-{(2S,6S)-6-[(E)-5-(tert-butyl-diphenyl-silanyloxy)-pent-1-enyl]-2-methoxy-5,6-dihydro-2H-pyran-2-yl}-5-((2S,3S,5R)-5-methoxy-3-triethylsilanyloxy-tetrahydro-furan-2-yl)-4-methyl-pentan-3-one 

Relevant academic research and scientific papers

Studies directed toward the total synthesis of azaspiracid. Construction of the C1-C19 carbon backbone and synthesis of the C10, C13 nonnatural transoidal bisspirocyclic ring system

The efficient entry to the C1-C19 carbon backbone of azaspiracid is outlined utilizing a key Julia coupling strategy. Spirocyclization of a C12 sulfone substrate induced formation of the unprecedented, nonnatural transoidal bisspiroketal. Construction of the bisspirocyclic array at C10 and C13, in the absence of the C12 sulfone, led to formation of the cisoidal orientation of the bisspirocycle, with the nonnatural stereochemistry at C13.

Controlling influences in bisspiroketal formation: Synthesis of the ABC ring system of azaspiracid

Substitution effects on the stereochemical outcome of bisspiroketalization on the C1-C17 carbon backbone of azaspiracid is presented. A possible explanation is offered to explain the observed stereochemical outcome.