921927-93-7

Usage

Uses

Used in Pharmaceutical Industry:
4-Thiazolecarboxylic acid, 2-[(1R,3R)-3-[[(2S,3S)-2-azido-3-methyl-1-oxopentyl]amino]-1-hydroxy-4-methylpentyl]-, methyl ester is used as a key intermediate in the synthesis of Tubulysin, a potent microtubule-depolymerizing agent with potential anticancer properties. Tubulysin has shown activity against various cancer cell lines, making this intermediate an important component in the development of new cancer therapies.
Additionally, the synthesis of 4-Thiazolecarboxylic acid, 2-[(1R,3R)-3-[[(2S,3S)-2-azido-3-methyl-1-oxopentyl]amino]-1-hydroxy- 4-methylpentyl]-, methyl ester and its derivatives may also contribute to the development of other bioactive molecules with potential applications in medicine, as its unique structure allows for further chemical modifications and exploration of its biological properties.

Upstream product

• 921927-92-6 (2S,3S)-2-azido-3-methylpentanoyl chloride 
• 921988-33-2 tubuvaline methyl ester 
• 159407-40-6 (2S,3S)-2-azido-3-methylpentanoic acid 
• 138754-84-4 N-benzyloxycarbonyl-L-valinal 
• 6216-65-5 N-benzyloxycarbonyl-L-valinol 
• 2026-48-4 (S)-valinol 
• 921927-99-3 methyl 2-(dimethoxymethyl)-4-thiazolecarboxylate 
• 73956-16-8 ethyl 2-(diethoxymethyl)-1,3-thiazole-4-carboxylate 
• 921927-90-4 methyl 2-((1R,3R)-3-((S)-1,1-dimethylethylsulfinamido)-1-hydroxy-4-methylpentyl)thiazole-4-carboxylate 
• 921927-89-1 methyl 2-((R,E)-3-(((S)-tert-butylsulfinyl)imino)-1-hydroxy-4-methylpentyl)thiazole-4-carboxylate 
• 921927-88-0 methyl 2-formylthiazole-4-carboxylate 
• 921927-91-5 methyl 2-((1R,3R)-3-amino-1-hydroxy-4-methylpentyl)thiazole-4-carboxylate hydrochloride 

Downstream Products

• 921927-98-2 desacetyl tubulysin D 
• 205304-87-6 Tybulysin-B 

Relevant academic research and scientific papers

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

Total syntheses of tubulysins

The total syntheses of tetrapeptides tubulysins D (1b), U (1c), and V (1d), which are potent tubulin polymerization inhibitors, are described. The synthesis of Tuv (2), an unusual amino acid constituent of tubulysins, includes an 1,3-dipolar cycloaddition

Expedient synthesis of N-methyl tubulysin analogues with high cytotoxicity

(Chemical Equation Presented) An optimized and highly efficient synthesis of potent, bioactive N-methyl tubulysin analogues 2 and 4 has been achieved with > 40% overall yields. This synthesis represents a significant improvement over previously reported s

The total synthesis of tubulysin D

The first total synthesis of tubulysin D is reported. The development and application of new tert-butanesulfinamide methods allowed for rapid syntheses of the tubuvaline and tubuphenylalanine fragments. Most significantly, a route was devised and implemen