667421-83-2

Upstream product

• 905589-27-7 (3S)-4-(tert-butyldiphenylsilyl)oxy-3-(triethylsilyl)oxy-butyraldehyde 
• 21204-67-1 methyl (triphenylphosphoranylidene)acetate 
• 58479-61-1 tert-butylchlorodiphenylsilane 
• 994-30-9 triethylsilyl chloride 

Downstream Products

• 680227-33-2 Acetic acid (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-ynyl ester 
• 667422-02-8 (3S,4S,5S)-6-[(2R,3R,5S)-3-tert-butyldimethylsiloxy-5-tert-butyldiphenylsiloxymethyloxolan-2-yl]-3-hydroxy-4-(2-methoxyethoxymethoxy)-5-(phenylmethoxymethyl)hexyl 2,2-dimethylpropanoate 
• 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 
• 680227-34-3 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 
• 667421-92-3 (2S,3S,4S)-1-[(2R,3R,5S)-3-tert-butyldimethylsiloxy-5-tert-butyldiphenylsiloxymethyloxolan-2-yl]-6-(4-methoxyphenylmethoxy)-2-phenylmethoxymethylhexane-3,4-diol 
• 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 
• 667422-00-6 (1S,2S)-1-[(4S)-2-(4-methoxyphenyl)1,3-dioxan-4-yl]-3-[(2R,3R,5S)-3-tert-butyldimethylsiloxy-5-tert-butyldiphenylsiloxymethyloxolan-2-yl]-2-phenylmethoxymethylpropan-1-ol 
• 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 
• 667422-01-7 (3S,4S,5S)-6-[(2R,3R,5S)-3-tert-butyldimethylsiloxy-5-tert-butyldiphenylsiloxymethyloxolan-2-yl]-4-(2-methoxyethoxymethoxy)-5-(phenylmethoxymethyl)hexane-1,3-diol 
• 667421-89-8 (4R)-3-{(2S)-3-[(2R,3R,5S)-5-tert-butyldiphenylsiloxymethyl-3-tert-butyldimethylsiloxyoxolan-2-yl]-2-phenylmethoxymethylpropanoyl}-4-benzyl-1,3-oxazolidin-2-one 
• 667421-78-5 (3S,4S,5S)-5-{[(2R,3R,5S)-3-tert-butyldimethylsiloxy-5-tert-butyldiphenylsiloxymethyloxolan-2-yl]methyl}-3,6-dihydroxy-4-(2-methoxyethoxymethoxy)hexyl 2,2-dimethylpropanoate 
• 667421-79-6 (3E)(5R)-6-[(2R,3R,5S)-3-tert-butyldimethylsiloxy-5-tert-butyldiphenylsiloxymethyloxolan-2-yl]-1-(4-methoxyphenylmethoxy)-5-phenylmethoxymethylhex-3-ene 
• 667421-77-4 (2R,3S,4R)-2-{4-[[(2R,3R,5S)-3-tert-butyldimethylsiloxy-5-tert-butyldiphenylsiloxymethyloxolan-2-yl]methyl]-3-(2-methoxyethoxymethoxy)thiolan-2-yl}ethyl 2,2-dimethylpropanoate 

Relevant academic research and scientific papers

Synthesis of the BCD ring system of azaspiracid: Construction of the trispiro ring structure by the thioether approach

The synthesis of the BCD ring system of azaspiracid 1 has been attained. Construction of the stereochemistry of the C13 position was successfully controlled by connection between the B ring and the C ring with a sulfur atom.

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.