537036-48-9

Upstream product

• 391235-55-5 (4R,5S)-2,2-di-tert-butyl-5-hydroxy-1,3-dioxa-2-silacyclohexane-4-methanol 
• 537036-24-1 (4R,5S)-4-[(2S,3R)-3-(2-benzyloxyethyl)-3-methyl-2-(toluene-4-sulfonyl)oxiranylmethyl]-2,2-di-tert-butyl-5-(triethylsilyloxy)-[1,3,2]dioxasilinane 
• 254442-52-9 Trifluoro-methanesulfonic acid (4R,5S)-2,2-di-tert-butyl-5-triethylsilanyloxy-[1,3,2]dioxasilinan-4-ylmethyl ester 
• 537036-25-2 (4aS,6R,8aR)-6-(2-benzyloxyethyl)-2,2-di-tert-butyl-6-methyldecahydro-1,3,5-trioxa-2-silanaphthalen-7-one 
• 100-39-0 benzyl bromide 
• 537036-47-8 (4aS,6R,7S,8aR)-6-(2-Benzyloxy-ethyl)-2,2-di-tert-butyl-6-methyl-hexahydro-1,3,5-trioxa-2-sila-naphthalen-7-ol 

Downstream Products

• 632354-38-2 (2S,3R,5S,6R)-5-benzyloxy-6-(2-benzyloxyethyl)-3-(tert-butyldimethylsilyloxy)-6-methyl-2-(prop-2-ynyl)tetrahydropyran 
• 632354-61-1 (2R,3S,5R,6S)-3-Benzyloxy-2-(2-benzyloxy-ethyl)-5-(tert-butyl-dimethyl-silanyloxy)-2-methyl-6-(3-trimethylsilanyl-prop-2-ynyl)-tetrahydro-pyran 
• 632354-32-6 trifluoromethanesulfonic acid (2S,3R,5S,6R)-5-benzyloxy-6-(2-benzyloxyethyl)-3-(tert-butyldimethylsilyloxy)-6-methyltetrahydropyran-2-ylmethyl ester 
• 632354-29-1 C₅₆H₈₈O₁₀Si₂ 
• 632354-59-7 C₅₆H₈₈O₁₂Si₂ 
• 537036-51-4 (2S,3R,4aS,6R,7S,8aR)-7-Benzyloxy-6-(2-benzyloxy-ethyl)-2-hydroxymethyl-6-methyl-octahydro-pyrano[3,2-b]pyran-3-ol 
• 537036-53-6 (2S,3R,4aS,6S,7R,8aS,9aR,10aR)-6-Benzyloxy-7-(2-benzyloxy-ethyl)-2-hydroxymethyl-7-methyl-decahydro-1,8,10-trioxa-anthracen-3-ol 
• 537036-27-4 Trifluoro-methanesulfonic acid (2S,3R,5S,6R)-5-benzyloxy-6-(2-benzyloxy-ethyl)-6-methyl-3-triethylsilanyloxy-tetrahydro-pyran-2-ylmethyl ester 
• 537036-30-9 (2S,4aS,6R,7S,8aR)-7-Benzyloxy-6-(2-benzyloxy-ethyl)-2-(tert-butyl-diphenyl-silanyloxymethyl)-6-methyl-hexahydro-pyrano[3,2-b]pyran-3-one 
• 537036-50-3 (2S,3R,4aS,6R,7S,8aR)-7-Benzyloxy-6-(2-benzyloxy-ethyl)-2-(tert-butyl-diphenyl-silanyloxymethyl)-6-methyl-octahydro-pyrano[3,2-b]pyran-3-ol 
• 537036-31-0 Trifluoro-methanesulfonic acid (2S,3R,4aS,6R,7S,8aR)-7-benzyloxy-6-(2-benzyloxy-ethyl)-6-methyl-3-triethylsilanyloxy-octahydro-pyrano[3,2-b]pyran-2-ylmethyl ester 
• 537036-33-2 (2S,4aS,6S,7R,8aS,9aR,10aR)-6-Benzyloxy-7-(2-benzyloxy-ethyl)-2-(tert-butyl-diphenyl-silanyloxymethyl)-7-methyl-octahydro-1,8,10-trioxa-anthracen-3-one 
• 537036-43-4 (2R,3S,4aR,5aS,6aR,7aS,10R,11S,12aR,13aS,14aR,15aS)-3-Benzyloxy-2-(2-benzyloxy-ethyl)-11-hydroxymethyl-2,10-dimethyl-octadecahydro-1,5,7,12,14-pentaoxa-cyclohepta[b]naphthacen-10-ol 
• 537036-52-5 (2S,3R,4aS,6S,7R,8aS,9aR,10aR)-6-Benzyloxy-7-(2-benzyloxy-ethyl)-2-(tert-butyl-diphenyl-silanyloxymethyl)-7-methyl-decahydro-1,8,10-trioxa-anthracen-3-ol 

Relevant academic research and scientific papers

Iterative synthesis of the ABCDEF-ring system of yessotoxin and adriatoxin

A stereocontrolled linear synthesis of the ABCDEF-ring system of yessotoxin and adriatoxin, diarrhetic shellfish toxins, is described. Iterative application of a tetrahydropyran synthesis by reaction of the alkylation of a sulfonyl-stabilized oxiranyl ani

Sulfonyl-Stabilized Oxiranyllithium-Based Approach to Polycyclic Ethers. Convergent Synthesis of the ABCDEF-Ring System of Yessotoxin and Adriatoxin

Convergent synthesis of the ABCDEF-ring system of yessotoxin and adriatoxin, marine polycyclic ether toxins causative of diarrheic shellfish poisoning, has been accomplished. The A-ring fragment was constructed by coupling of an appropriately functionalized sulfonyl-stabilized oxiranyl anion and a triflate prepared from an erythritol derivative. An iterative protocol of the oxiranyl anion strategy was also applied for the construction of the DEF-ring fragment. The triflate derivatives of the A-ring and the DEF-ring fragments were connected with lithium acetylide. The resulting acetylene derivative was further transformed into the hexacyclic ABCDEF fragment via oxidation of the acetylene unit to 1,2-diketone, double methyl acetal formation, and reductive etherification.