667422-01-7

Upstream product

• 3587-60-8 Benzyloxymethyl chloride 
• 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 
• 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 
• 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 
• 667421-79-6 (3E)(5R)-6-[(2R,3R,5S)-3-tert-butyldimethylsiloxy-5-tert-butyldiphenylsiloxymethyloxolan-2-yl]-1-(4-methoxyphenylmethoxy)-5-phenylmethoxymethylhex-3-ene 
• 667421-88-7 (4R)-3-{3-[(2R,3R,5S)-5-tert-butyldiphenylsiloxymethyl-3-tert-butyldimethylsiloxyoxolan-2-yl]propanoyl}-4-benzyl-1,3-oxazolidin-2-one 
• 667421-90-1 (2R)-3-[(2R,3R,5S)-5-tert-butyldiphenylsiloxymethyl-3-tert-butyldimethylsiloxyoxolan-2-yl]-2-phenylmethoxymethylpropan-1-ol 
• 667421-86-5 methyl (2E)-3-{3-[(2S)-3-tert-butyldiphenylsiloxy-2-triethylsiloxypropyl](2S,3R)oxiran-2-yl}prop-2-enoate 
• 680227-39-8 methyl 3-[(2R,3R,5S)-5-tert-butyldiphenylsiloxymethyl-3-tert-butyldimethylsiloxyoxolan-2-yl]propanoate 
• 667421-87-6 3-[(2R,3R,5S)-5-tert-butyldiphenylsiloxymethyl-3-tert-butyldimethylsiloxyoxolan-2-yl]propanoic acid 
• 667421-99-0 methyl (2E)-3-[(2R,3R,5S)-5-tert-butyldiphenylsiloxymethyl-3-tert-butyldimethylsiloxyoxolan-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 
• 667421-84-3 (2E,5S)-6-tert-butyldiphenylsiloxy-5-triethylsiloxyhex-2-en-1-ol 

Downstream Products

• 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 
• 667421-76-3 {(1S,3R,5S,7R,9R,12R)-2,6,15-trioxa-11-thiatetracyclo[7.6.0.0^1,12.0^3,7]pentadec-5-yl}tert-butyldiphenylsiloxymethane 
• 667421-98-9 2-[(1R,3S,4R,7R,9R,11S)-11-tert-butyldiphenylsiloxymethyl-3-methoxy-2,10-dioxa-5-thiatricyclo[7.3.0.0^3,7]dodec-4-yl]ethan-1-ol 
• 667421-95-6 (2R,3S,4R)-2-{4-[[(2R,3R,5S)-3-tert-butyldimethylsiloxy-5-tert-butyldiphenylsiloxymethyloxolan-2-yl]methyl]-3-hydroxythiolan-2-yl}ethyl 2,2-dimethylpropanoate 
• 667421-96-7 2-{(2R,4R)-4-[[(2R,3R,5S)-3-tert-butyldimethylsiloxy-5-tert-butyldiphenylsiloxymethyloxolan-2-yl]methyl]-3-oxo-2-(2,4,5-trihydrothienyl)}ethyl 2,2-dimethylpropanoate 
• 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 
• 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 
• 667421-94-5 (3S,4S,5S)-5-{[(2R,3R,5S)-3-tert-butyldimethylsiloxy-5-tert-butyldiphenylsiloxymethyloxolan-2-yl]methyl}-3,6-bis(methanesulfonyloxy)-4-(2-methoxyethoxymethoxy)hexyl 2,2-dimethylpropanoate 

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.

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.