725250-94-2

Upstream product

• 725250-93-1 (2S,4R)-5-(tert-Butyl-diphenyl-silanyloxy)-4-methoxy-2-methyl-pentanoic acid methoxy-methyl-amide 

Downstream Products

• 725250-96-4 {(E)-(2R,4R,8S,11R)-11-[(4R,5R,6R)-6-(2-Benzyloxy-ethyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-2,8-dimethoxy-4,7-dimethyl-dodec-6-enyloxy}-tert-butyl-diphenyl-silane 
• 725250-95-3 (E)-(2R,9R,11R)-2-[(4R,5R,6R)-6-(2-Benzyloxy-ethyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-12-(tert-butyl-diphenyl-silanyloxy)-11-methoxy-6,9-dimethyl-dodec-6-en-5-one 
• 725250-99-7 (2E,4E)-6-{(4R,5R,6R)-6-[(E)-(1R,4S,8R,10R)-11-(tert-Butyl-diphenyl-silanyloxy)-4,10-dimethoxy-1,5,8-trimethyl-undec-5-enyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-hexa-2,4-dienoic acid methyl ester 
• 725250-97-5 2-{(4R,5R,6R)-6-[(E)-(1R,4S,8R,10R)-11-(tert-Butyl-diphenyl-silanyloxy)-4,10-dimethoxy-1,5,8-trimethyl-undec-5-enyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-ethanol 
• 725250-98-6 {(4R,5R,6R)-6-[(E)-(1R,4S,8R,10R)-11-(tert-Butyl-diphenyl-silanyloxy)-4,10-dimethoxy-1,5,8-trimethyl-undec-5-enyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-acetaldehyde 
• 725251-02-5 (E)-(2R,4R,8S,11R)-11-[(4R,5R,6R)-6-(2-Benzyloxy-ethyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-2,8-dimethoxy-4,7-dimethyl-dodec-6-enal 
• 1027025-42-8 (3S,5R)-6-(tert-Butyl-diphenyl-silanyloxy)-5-methoxy-3-methyl-hexanal 

Relevant academic research and scientific papers

Synthesis of the C1-C27 portion of the aplyronines

This manuscript describes the use of the anti,anti-diastereoselective aldol reaction of an efficiently generated dipropionate equivalent to construct the C5-C14-portion of the aplyronines. This portion was then coupled with a compound corresponding to C15-C20 of the targets. Further elaboration and an additional coupling led to an intermediate containing C1-C27 with appropriate stereochemistry and functionalization for eventual conversion into the aplyronines.