391198-99-5

Upstream product

• 18162-48-6 tert-butyldimethylsilyl chloride 
• 100-39-0 benzyl bromide 
• 124605-10-3 (+/-)-methyl bishomononactate 
• 468057-25-2 C₁₃H₂₄O₄ 
• 391198-95-1 (+)-benzyl (2S,3S,6R,8S)-8-O-[(2'R,3'R,6'S,8'R)-8'-O'-(tert-butyldimethylsilyl)bishomononactoyl]bishomononactate 
• 391198-97-3 (S)-2-{(2S,5R)-5-[(S)-2-((R)-2-{(2R,5S)-5-[(R)-2-(tert-Butyl-dimethyl-silanyloxy)-3-methyl-butyl]-tetrahydro-furan-2-yl}-propionyloxy)-3-methyl-butyl]-tetrahydro-furan-2-yl}-propionic acid 
• 391198-94-0 (R)-2-{(2R,5S)-5-[(R)-2-(tert-Butyl-dimethyl-silanyloxy)-3-methyl-butyl]-tetrahydro-furan-2-yl}-propionic acid 
• 391198-92-8 benzyl (2S,3S,6R,8S)-3,6-epoxy-2,9-dimethyl-8-hydro-xydecanoate 
• 391198-93-9 (-)-bishomononactic acid 
• 391198-91-7 (+)-bishomononactic acid 
• 391198-96-2 (-)-benzyl (2S,3S,6R,8S)-8-O-[(2'R,3'R,6'S,8'R)-bishomononactoyl]bishomononactate 
• 391198-98-4 (+)-S-2-pyridyl (2S,3S,6R,8S)-[(2'R,3'R,6'S,8'R)-8'-O'-tert-buthydimethylsilylbishomononactoyl]thiobishomononactate 

Relevant academic research and scientific papers

Synthesis of macrotetrolide α, a designed polynactin analog composed of bishomononactic acids

Macrotetrolide α (1), a designed polynactin analog composed of (+)- and (-)-bishomononactic acids, was synthesized. The monomeric acids were prepared using cis-selective iodoetherification and optical resolution of the corresponding O-acetylmandelates as the key steps. Esterification and macrolactonization of the monomers were performed by Corey-Mukaiyama-Gerlach method. Compound 1 showed no immunosuppressive activity contrary to other natural polynactin congeners.

Synthesis of Macrotetrolide α, a Designed Polynactin Analog Composed of (+)- and (-)-Bishomononactic Acids

Macrotetrolide α, a designed analog of polynactin composed of (+)- and (-)-bishomononactic acids, was synthesized. These monomers were prepared via optical resolution of the corresponding (S)-O-acetylmandelates. Assembly of the monomers to macrotetrolide a look seven steps without any loss of the intermediates.