844439-31-2

Upstream product

• 101711-78-8 (3R)-3-propionyl-4-benzyloxazolidin-2-one 
• 279227-20-2 (2S)-5-benzyloxy-2-methyl-1-pentanal 
• 81678-40-2 (2S)-5-(benzyloxy)-2-methylpentan-1-ol 

Downstream Products

• 844439-45-8 (R)-4-Benzyl-3-[(8Z,12E)-(2R,3S,4S,11S)-3-(tert-butyl-dimethyl-silanyloxy)-2,4,8,12-tetramethyl-13-(2-methyl-thiazol-4-yl)-11-triethylsilanyloxy-trideca-8,12-dienoyl]-oxazolidin-2-one 
• 844439-35-6 (R)-4-Benzyl-3-[(8Z,12E)-(2R,3S,4S,11S)-3,11-bis-(tert-butyl-dimethyl-silanyloxy)-2,4,8,12-tetramethyl-13-(2-methyl-thiazol-4-yl)-trideca-8,12-dienoyl]-oxazolidin-2-one 
• 844439-34-5 (R)-4-Benzyl-3-[(2R,3S,4S)-3-(tert-butyl-dimethyl-silanyloxy)-7-iodo-2,4-dimethyl-heptanoyl]-oxazolidin-2-one 
• 844439-33-4 (R)-4-Benzyl-3-[(2R,3S,4S)-3-(tert-butyl-dimethyl-silanyloxy)-7-hydroxy-2,4-dimethyl-heptanoyl]-oxazolidin-2-one 
• 844439-32-3 (R)-4-Benzyl-3-[(2R,3S,4S)-7-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-2,4-dimethyl-heptanoyl]-oxazolidin-2-one 

Relevant academic research and scientific papers

Synthesis of 4-aza analogs of epothilone D

An efficient synthesis of epothilone D analogs of type 1 has been developed, which is based on a highly diastereoselective Evans aldol reaction as one of the key steps. A profound difference in the relative stabilities of TBS-protecting groups on C7-O and C15-O was observed between secondary and primary amide groups at C5-N4. Although modeling studies had suggested analogs of type 1 to assume a conformation similar to the NMR-derived conformation of tubulin-bound epothilone A, compounds 1a-d were found to be significantly less active than the parent compound epothilone D.