328535-20-2

Upstream product

• 328535-18-8 1-[(2R,4aR,6R,7R,8R,8aR)-8-Benzyloxy-7-(tert-butyl-dimethyl-silanyloxy)-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl]-hept-6-en-3-one 
• 328534-81-2 1-[(2R,4aR,6R,7R,8R,8aR)-8-Benzyloxy-7-(tert-butyl-dimethyl-silanyloxy)-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl]-hept-6-en-3-ol 
• 328535-19-9 (2R,3R,4R,4aR,6R,8aR)-4-Benzyloxy-6-but-3-enyl-2-(tert-butyl-dimethyl-silanyloxymethyl)-6-methoxy-octahydro-pyrano[3,2-b]pyran-3-ol 
• 194039-11-7 3-[(2R,4aR,6R,7R,8R,8aR)-8-Benzyloxy-7-(tert-butyl-dimethyl-silanyloxy)-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl]-propionaldehyde 

Downstream Products

• 1335029-06-5 (2R)-3-((2S,5R,6R,8S)-5-(benzyloxy)-8-((R,E)-4-((2R,4a'R,5R,6'S,8'R,8a'R)-8'-(benzyloxy)-6'-((1S,3S)-1-(benzyloxy)-3-((2S,6R,11S)-11-methyl-1,7-dioxaspiro[5.5]undecan-2-yl)butyl)-7'-methyleneoctahydro-3H,3'H-spiro[furan-2,2'-pyrano[3,2-b]pyran]-5-yl)but-3-en-2-yl)-10-methyl-1,7-dioxaspiro[5.5]undec-10-en-2-yl)-2-hydroxy-2-methylpropanoic acid 
• 1335029-05-4 (2R)-3-((2S,5R,6R,8S)-5-(benzyloxy)-8-((R,E)-4-((2R,4a'R,5R,6'S,8'R,8a'R)-8'-(benzyloxy)-6'-((1S,3S)-1-(benzyloxy)-3-((2S,6R,11S)-11-methyl-1,7-dioxaspiro[5.5]undecan-2-yl)butyl)-7'-methyleneoctahydro-3H,3'H-spiro[furan-2,2'-pyrano[3,2-b]pyran]-5-yl)but-3-en-2-yl)-10-methyl-1,7-dioxaspiro[5.5]undec-10-en-2-yl)-2-methylpropane-1,2-diol 
• 1335028-84-6 (6R,E)-6-((2S,6R,8S,11R)-11-(benzyloxy)-4-methyl-8-(((R)-2,2,4-trimethyl-1,3-dioxolan-4-yl)methyl)-1,7-dioxaspiro[5.5]undec-4-en-2-yl)-1-((2S,4aR,6S,8R,8aR)-8-(benzyloxy)-6-((1S,3S)-1-(benzyloxy)-3-((2S,6R,11S)-11-methyl-1,7-dioxaspiro[5.5]undecan-2-yl)butyl)-2-methoxy-7-methyleneoctahydropyrano[3,2-b]pyran-2-yl)hept-4-en-3-one 
• 1335028-86-8 dimethyl (4-((2S,4aR,6S,8R,8aR)-8-(benzyloxy)-6-((1S,3S)-1-(benzyloxy)-3-((2S,6R,11S)-11-methyl-1,7-dioxaspiro[5.5]undecan-2-yl)butyl)-2-methoxy-7-methyleneoctahydropyrano[3,2-b]pyran-2-yl)-2-oxobutyl)phosphonate 
• 1335029-04-3 3-((2S,4aR,6S,8R,8aR)-8-(benzyloxy)-6-((1S,3S)-1-(benzyloxy)-3-((2S,6R,11S)-11-methyl-1,7-dioxaspiro[5.5]undecan-2-yl)butyl)-2-methoxy-7-methyleneoctahydropyrano[3,2-b]pyran-2-yl)propanal 
• 1335029-03-2 (2R,4aR,6S,8R,8aR)-8-(benzyloxy)-6-((1S,3S)-1-(benzyloxy)-3-((2S,6R,11S)-11-methyl-1,7-dioxaspiro[5.5]undecan-2-yl)butyl)-2-(but-3-en-1-yl)-2-methoxy-7-methyleneoctahydropyrano[3,2-b]pyran 
• 1335028-87-9 C₂₂H₂₈O₅ 
• 1335029-13-4 (1R,3S)-1-((2S,4R,4aR,6R,8aR)-4-(benzyloxy)-6-(but-3-en-1-yl)-6-methoxy-3-methyleneoctahydropyrano[3,2-b]pyran-2-yl)-3-((2S,6R,11S)-11-methyl-1,7-dioxaspiro[5.5]undecan-2-yl)butan-1-ol 
• 1335029-02-1 (1S,3S)-1-((2S,4R,4aR,6R,8aR)-4-(benzyloxy)-6-(but-3-en-1-yl)-6-methoxy-3-methyleneoctahydropyrano[3,2-b]pyran-2-yl)-3-((2S,6R,11S)-11-methyl-1,7-dioxaspiro[5.5]undecan-2-yl)butan-1-ol 
• 1335029-12-3 ((2S,4R,4aR,6R,8aR)-4-(benzyloxy)-6-(but-3-en-1-yl)-6-methoxy-3-methyleneoctahydropyrano-[3,2-b]pyran-2-yl)methanol 
• 1335029-19-0 (2S)-3-((2S,5R,6R,8S)-5-(benzyloxy)-8-((R,E)-4-((2R,4a'R,5R,6'S,8'R,8a'R)-8'-(benzyloxy)-6'-((1S,3S)-1-(benzyloxy)-3-((2S,6R,11S)-11-methyl-1,7-dioxaspiro[5.5]undecan-2-yl)butyl)-7'-methyleneoctahydro-3H,3'H-spiro[furan-2,2'-pyrano[3,2-b]pyran]-5-yl)but-3-en-2-yl)-10-methyl-1,7-dioxaspiro[5.5]undec-10-en-2-yl)-2-hydroxy-2-methylpropanoic acid 
• 1335029-18-9 (2S)-3-((2S,5R,6R,8S)-5-(benzyloxy)-8-((R,E)-4-((2R,4a'R,5R,6'S,8'R,8a'R)-8'-(benzyloxy)-6'-((1S,3S)-1-(benzyloxy)-3-((2S,6R,11S)-11-methyl-1,7-dioxaspiro[5.5]undecan-2-yl)butyl)-7'-methyleneoctahydro-3H,3'H-spiro[furan-2,2'-pyrano[3,2-b]pyran]-5-yl)but-3-en-2-yl)-10-methyl-1,7-dioxaspiro[5.5]undec-10-en-2-yl)-2-methylpropane-1,2-diol 
• 1335029-17-8 (6R,E)-6-((2S,6R,8S,11R)-11-(benzyloxy)-4-methyl-8-(((S)-2,2,4-trimethyl-1,3-dioxolan-4-yl)methyl)-1,7-dioxaspiro[5.5]undec-4-en-2-yl)-1-((2S,4aR,6S,8R,8aR)-8-(benzyloxy)-6-((1S,3S)-1-(benzyloxy)-3-((2S,6R,11S)-11-methyl-1,7-dioxaspiro[5.5]undecan-2-yl)butyl)-2-methoxy-7-methyleneoctahydropyrano[3,2-b]pyran-2-yl)hept-4-en-3-one 

Relevant academic research and scientific papers

Expedient access to the okadaic acid architecture: A novel synthesis of the C1-C27 domain

A newly designed synthetic entry to the C1-C27 domain of okadaic acid has been developed. This incorporates substantial improvements in the preparations of the key okadaic acid building blocks representing the C3-C8, C9-C14, and C16-C27 portions. The synthesis of the C3-C8 lactone used (R)-glycidol as the origin of the C4 stereogenic center and featured a late-stage optional incorporation of the C7 hydroxyl group. The complementary C9-C14 fragment was synthesized in a concise route from (R)-3-tert-butyldimethylsilyloxy-2-methylpropanal and propargyl bromide. Assembly of the C3-C14 spiroketal-containing intermediate from the constituent fragments revealed a dramatic effect of C7 functionalization upon spiroketalization efficiency. In contrast, both (9E)- and (9Z)-enones converged readily to the C8 spiroketal upon treatment with acid. Modifications to the central C16-C27 fragment of okadaic acid included the early replacement of benzylic protecting groups by more suitable functionalities to facilitate both the generation of the C15-C27 intermediate and the deprotection of the final products. These modular building blocks were deployed for the synthesis of the C1-C27 scaffold of 7-deoxyokadaic acid. This work demonstrates improvements in the formation of versatile okadaic acid intermediates, as well as a reordering of fragment couplings. This alternative order of coupling was designed to promote the late stage incorporation of nonnatural lipophilic extensions from the C27 terminus.