796039-47-9

Upstream product

• 244033-72-5 (4S)-4-N-tert-butoxycarbonylamino-5-phenyl-2-methyl-2-trans-pentenoic acid, ethyl ester 
• 3182-95-4 L-Phenylalaninol 
• 24424-99-5 di-tert-butyl dicarbonate 
• 944559-43-7 (R)-4-(tert-butoxycarbonylamino)-2-methyl-5-phenylpentanoic acid 
• 773155-79-6 N-((1R,3S)-1-Benzyl-4-hydroxy-3-methyl-butyl)-2,2,2-trifluoro-acetamide 
• 862387-31-3 (S)-4-(tert-Butyl-dimethyl-silanyloxy)-3-methyl-butyric acid 
• 204917-42-0 (3S)-4-(tert-butyldimethylsilanyloxy)-3-methylbutyraldehyde 
• 156592-93-7 (3S)-4-<(tert-butyldimethylsilyl)oxy>-3-methylbutanol 
• 1174764-18-1 (S)-ethyl 4-(tert-butoxycarbonylamino)-2-methyl-5-phenylpent-2-enoate 
• 87694-53-9 Boc-Phe-OH N,O-dimethyl hydroxamate 
• 13734-34-4 N-tert-butoxycarbonyl-L-phenylalanine 
• 356788-71-1 [L-(trans)]-4-[(t-butoxycarbonyl)amino]-2-methyl-5-phenyl-2-pentenoic acid 
• 72155-45-4 Boc-L-phenylalaninal 
• 66605-57-0 (S)-N-tert-butoxycarbonyl-2-amino-3-phenylpropanol 

Downstream Products

• 936691-37-1 [1-benzyl-4-(tert-butyl-diphenyl-silanyloxy)-3-methyl-butyl]-carbamic acid tert-butyl ester 
• 368870-65-9 (2S,4R)-4-((tert-butoxycarbonyl)amino)-2-methyl-5-phenylpentanoic acid 
• 1101181-32-1 C₄₂H₅₉N₅O₆S 
• 1101181-34-3 C₄₀H₅₆N₄O₇S 
• 1017624-85-9 (R)-4-tert-butoxycarbonylamino-3-methyl-5-phenylpentanoic acid benzyl ester 

Relevant academic research and scientific papers

Diastereocontrol in Radical Addition to β-Benzyloxy Hydrazones: Revised Approach to Tubuvaline and Synthesis of O-Benzyltubulysin v Benzyl Ester

Radical addition to chiral N-acylhydrazones has generated unusual amino acids tubuphenylalanine (Tup) and tubuvaline (Tuv) that are structural components of the tubulysin family of picomolar antimitotic agents and previously led to a tubulysin tetrapeptide analog with a C-terminal alcohol. To improve efficiency in this synthetic route to tubulysins, and to address difficulties in oxidation of the C-terminal alcohol, here we present two alternative routes to Tuv that (a) improve step economy, (b) provide modified conditions for Mn-mediated radical addition in the presence of aromatic heterocycles, and (c) expose an example of double diastereocontrol in radical addition to a β-benzyloxyhydrazone with broader implications for asymmetric amine synthesis via radical addition. An efficient coupling sequence affords 11-O-benzyltubulysin V benzyl ester.

Total synthesis of tubulysin U and N14-desacetoxytubulysin H

A concise and efficient procedure for the total synthesis of tubulysin U and N14-desacetoxytubulysin H has been developed with high stereoselectivity on a gram scale. This synthesis features an elegant cascade one-pot process to install the challenging th

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.

TUBULYSIN DERIVATIVES

Novel tubulysin derivatives which may be useful as cytotoxic agents to provide therapeutic benefits in the treatment of various types of cancers, alone or as drug conjugates with antibodies are provided. The tubulysin derivatives consist of a tetrapeptide scaffold comprising methyl and ethyl substituted piperidines. The tubulysin conjugates further comprise monoclonal antibody via succinimide linkers.

Synthesis of the tubuvaline-tubuphenylalanine (Tuv-Tup) fragment of tubulysin

(Chemical Equation Presented) Advanced intermediates and analogues of tubulysins were prepared in a convergent strategy.