1101181-34-3

Upstream product

• 368870-65-9 (2S,4R)-4-((tert-butoxycarbonyl)amino)-2-methyl-5-phenylpentanoic acid 
• 1467751-12-7 tert-butyl (3R,5R)-5-(tert-butyldimethylsilyloxy)-6-hydroxy-2-methylhexan-3-ylcarbamate 
• 156592-93-7 (3S)-4-<(tert-butyldimethylsilyl)oxy>-3-methylbutanol 
• 13139-16-7 N-(tert-butyloxycarbonyl)-L-isoleucine 
• 796039-47-9 (1R,3S)-(1-benzyl-4-hydroxy-3-methylbutyl)carbamic acid tert-butyl ester 
• 1017624-85-9 (R)-4-tert-butoxycarbonylamino-3-methyl-5-phenylpentanoic acid benzyl ester 
• 204917-42-0 (3S)-4-(tert-butyldimethylsilanyloxy)-3-methylbutyraldehyde 
• 862387-31-3 (S)-4-(tert-Butyl-dimethyl-silanyloxy)-3-methyl-butyric acid 

Relevant academic research and scientific papers

An enantioselective total synthesis of tubulysin V

Tubulysin V has been enantioselectively synthesized from the units of dipeptide 23, Tuv and Tup. The features of this synthetic strategy is included three portions, the Tuv fragment 17 was diastereoselectively synthesized from the D-malic acid, the stereocenters of the Tup unit was constructed by the asymmetric reduction as well as methylation, and the epimerization for several known methods was successfully avoided by condensation of fragment 19 with 24, and by deprotection with hydrogenation.

Total synthesis and biological evaluation of tubulysin U, tubulysin V, and their analogues

A stereoselective total synthesis of the cytotoxic natural products tubulysin U, tubulysin V, and its unnatural epimer epitubulysin V, is reported. Simplified analogues containing N,N-dimethyl- D-alanine as a replacement for the N-terminal N-Me-pipecolinic acid residue of the tubulysins are also disclosed. Biological evaluation of these natural products and analogues provided key information with regard to structural and stereochemical requirements for antiproliferative activity and tubulin polymerization inhibition.