680227-33-2

Upstream product

• 108-24-7 acetic anhydride 
• 680227-32-1 (R)-8-Benzyloxy-1-[(2S,3aR,5S,6R,7aR)-2-(tert-butyl-diphenyl-silanyloxymethyl)-5-methoxy-6-methyl-hexahydro-furo[3,2-b]pyran-5-yl]-7-triethylsilanyloxy-oct-4-yn-3-ol 
• 667421-82-1 methyl (3S)-4-tert-butyldiphenylsiloxy-3-triethylsiloxybutanoate 
• 667421-86-5 methyl (2E)-3-{3-[(2S)-3-tert-butyldiphenylsiloxy-2-triethylsiloxypropyl](2S,3R)oxiran-2-yl}prop-2-enoate 
• 667421-85-4 {3-[(2S)-3-tert-butyldiphenylsiloxy-2-triethylsiloxypropyl](2S,3R)oxiran-2-yl}-methanol 
• 667421-83-2 methyl (2E,5S)-6-tert-butyldiphenylsiloxy-5-triethylsiloxyhex-2-enoate 
• 680227-30-9 3-{(1R,3S,4R,6R,8S)-8-tert-butyldiphenylsiloxymethyl-3-methoxy-4-methyl-2,7-dioxabicyclo[4.3.0]non-3-yl}-propanal 
• 680227-29-6 (1R,3S,4R,6R,8S)-8-tert-butyldiphenylsiloxymethyl-3-methoxy-4-methyl-3-(prop-2-enyl)-2,7-dioxabicyclo[4.3.0]nonane 
• 667421-84-3 (2E,5S)-6-tert-butyldiphenylsiloxy-5-triethylsiloxyhex-2-en-1-ol 
• 667421-80-9 methyl (2E)-3-[(2R,3R,5S)-5-tert-butyldiphenylsiloxymethyl-3-hydroxyoxolan-2-yl]prop-2-enoate 
• 680227-27-4 (1R,6R,8S)-8-tert-butyldiphenylsiloxymethyl-2,7-dioxabicyclo[4.3.0]nonan-3-one 
• 58479-61-1 tert-butylchlorodiphenylsilane 
• 994-30-9 triethylsilyl chloride 
• 680227-42-3 3-[(2S,3aR,5S,6R,7aR)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-methoxy-6-methyl-hexahydro-furo[3,2-b]pyran-5-yl]-propan-1-ol 

Downstream Products

• 680227-36-5 Acetic acid (Z)-(R)-6-benzyloxy-1-{2-[(2S,3aR,5R,6R,7aR)-2-(tert-butyl-diphenyl-silanyloxymethyl)-6-methyl-5-methylsulfanyl-hexahydro-furo[3,2-b]pyran-5-yl]-ethyl}-5-triethylsilanyloxy-hex-2-enyl ester 
• 680227-37-6 (Z)-(R)-8-Benzyloxy-1-[(2S,3aR,5R,6R,7aR)-2-(tert-butyl-diphenyl-silanyloxymethyl)-6-methyl-5-methylsulfanyl-hexahydro-furo[3,2-b]pyran-5-yl]-7-triethylsilanyloxy-oct-4-en-3-ol 
• 680227-25-2 (7R)-1-[(1R,3R,4R,6R,8S)-8-tert-butyldiphenylsiloxymethyl-3-methylthio-4-methyl-2,7-dioxabicyclo[4.3.0]non-3-yl](4Z)-7-triethylsiloxy-8-phenylmetoxyoct-4-en-3-one 
• 680227-35-4 Acetic acid (Z)-(R)-6-benzyloxy-1-{2-[(2S,3aR,5R,6R,7aR)-2-(tert-butyl-diphenyl-silanyloxymethyl)-6-methyl-5-methylsulfanyl-hexahydro-furo[3,2-b]pyran-5-yl]-ethyl}-5-hydroxy-hex-2-enyl ester 
• 680227-34-3 Acetic acid (Z)-(R)-6-benzyloxy-1-{2-[(2S,3aR,5S,6R,7aR)-2-(tert-butyl-diphenyl-silanyloxymethyl)-5-methoxy-6-methyl-hexahydro-furo[3,2-b]pyran-5-yl]-ethyl}-5-triethylsilanyloxy-hex-2-enyl ester 

Relevant academic research and scientific papers

Synthetic studies on azaspiracid, a novel shellfish poison: Attempts to construct the ABCD ring system

Synthesis of the ABCD ring system of azaspiracid (1) was attempted. Construction of the highly substituted tetrahydrofuran (9) via the Pd(0)-mediated cyclization, followed by spirocyclization afforded trispiro-ring (28), carrying an unnatural ring-junctions. The BCD ring system of I was successfully produced by using the bridge of a sulfur atom between the B and C ring to control the spiroacetal center of the C13 position. The stereostructures were unambiguously determined by the NOE experiments.