120205-57-4

Upstream product

• 540-88-5 acetic acid tert-butyl ester 
• 120205-56-3 N-Z-N-Me-(S,R)-isoleucinal 
• 120205-56-3 benzyl methyl[(2S,3S)-3-methyl-1-oxopentan-2-yl]carbamate 
• 42417-66-3 (2S,3S)-3-methyl-2-(methyl{[(phenylmethyl)oxy]carbonyl}amino)pentanoic acid 
• 120205-55-2 benzyl [(2S,3S)-1-hydroxy-3-methylpentan-2-yl]methylcarbamate 
• 3160-59-6 N-Cbz-L-Isoleucine 
• 501-53-1 benzyl chloroformate 
• 120205-55-2 N-Z-N-Me-(S,R)-isoleucinol 
• 163887-30-7 N-Z-N-Me-(S,R)-Ile 
• 319-78-8 isoleucine 
• 3160-59-6 N-benzyloxycarbonyl-isoleucine 

Downstream Products

• 120205-52-9 tert-butyl (3R,4S,5S)-4-[(2S)-2-[[(benzyloxy)carbonyl]amino]-N,3-dimethylbutanamido]-3-methoxy-5-methylheptanoate 
• 120205-53-0 (3R,4S,5S)-tert-butyl 4-((S)-2-((S)-2-(dimethylamino)-3-methylbutanamido)-N,3-dimethylbutanamido)-3-methoxy-5-methylheptanoate 
• 120205-48-3 tert-Butyl (3R,4S,5S)-3-methoxy-4-(N-methylamino)-5-methylheptanoate hydrochloride 
• 110417-88-4 dolastatin 10 
• 154633-73-5 tert-Butyl (3S,4S,5S)-3-methoxy-4--5-methylheptanoate 

Relevant academic research and scientific papers

The dolastatins. 19. Synthesis of dolaisoleuine

The synthesis of dolaisoleuine as its tert-butyl ester (Dil-OBu(t)), a β- methoxy-γ-amino acid component of dolastatin 10, has been achieved employing as key step an aldol condensation between N-(benzyloxycarbonyl)-N-methyl- (S,S)-isoleucinal and tert-butyl acetate followed by O-methylation. The overall six-step reaction sequence to Dil proved to be convenient for routine preparation of this new amino acid and its stereochemical assignment as (3R,4S,5S)-N,O-dimethylisostatine.

An expeditious synthesis of dolastatin 10

Total synthesis of dolastatin 10 (1) was completed by developing an efficient synthesis of two key amino acid components, Dil (6) and Dap (11), and subsequent stepwise coupling of five amino acid components from C-terminal Doe.