919518-38-0

Upstream product

• 72155-45-4 Boc-L-phenylalaninal 
• 87694-53-9 Boc-Phe-OH N,O-dimethyl hydroxamate 
• 24424-99-5 di-tert-butyl dicarbonate 
• 1423040-33-8 (S)-tert-butyl 5-benzyl-3-methylene-2-oxopyrrolidine-1-carboxylate 
• 186581-53-3 diazomethane 
• 368870-65-9 (2S,4R)-4-((tert-butoxycarbonyl)amino)-2-methyl-5-phenylpentanoic acid 
• 368870-63-7 (3R,5R)-tert-butyl 5-benzyl-3-methyl-2-oxopyrrolidine-1-carboxylate 
• 74-88-4 methyl iodide 
• 109579-08-0 (S)-[1-benzyl-2-(2,2-dimethyl-4,6-dioxo-[1,3]dioxan-5-yl)-2-oxo-ethyl]-carbamic acid tert-butyl ester 
• 197006-05-6 (R)-[1-benzyl-2-(2,2-dimethyl-4,6-dioxo-[1,3]dioxan-5-yl)-ethyl]-carbamic acid tert-butyl ester 
• 13734-34-4 N-tert-butoxycarbonyl-L-phenylalanine 
• 362495-79-2 [2S,4R,1'S,2'S]-(+)-N,2-dimethyl-5-phenyl-N-(2'-phenyl-2'-hydroxy-1'-methylethyl)-4-(p-toluenesulfonylamino)pentanamide 
• 362495-90-7 [2S,4R]-(-)-2-methyl-5-phenyl-4-(p-toluenesulfonylamino)pentanoic acid 
• 362496-00-2 [2S,4R]-(-)-methyl 2-methyl-5-phenyl-4-(p-toluenesulfonylamino)pentanoate 

Downstream Products

• 919518-59-5 methyl (2S,4R)-4-{[(2-{(1R,3R)-3-[(tert-butoxycarbonyl)amino]-1-hydroxy-4-methylpentyl}-1,3-thiazol-4-yl)carbonyl]amino}-2-methyl-5-phenylpentanoate 
• 1423040-35-0 methyl (2S,4R)-4-{[(2-{(1R,3R)-1-acetoxy-3-[(tert-butoxycarbonyl)amino]-4-methylpentyl}-1,3-thiazol-4-yl)carbonyl]amino}-2-methyl-5-phenylpentanoate 
• 1423040-49-6 methyl (2S,4R)-4-{[(2-{(6S,9R,11R)-6-[(2S)-butan-2-yl]-9-isopropyl-2,2-dimethyl-4,7,13-trioxo-3,12-dioxa-5,8-diazatetradecan-11-yl}-1,3-thiazol-4-yl)carbonyl]amino}-2-methyl-5-phenylpentanoate 
• 1423040-36-1 (R)-benzyl 2-((2S,3S)-1-((1R,3R)-1-acetoxy-1-(4-((2R,4S)-5-methoxy-4-methyl-5-oxo-1-phenylpentan-2-ylcarbamoyl)thiazol-2-yl)-4-methylpentan-3-ylamino)-3-methyl-1-oxopentan-2-ylcarbamoyl)piperidine-1-carboxylate 
• 919518-62-0 methyl (2S,4R)-4-[({2-[(1R,3R)-1-acetoxy-4-methyl-3-{[(2S,3S)-3-methyl-2-({[(2R)-1-methylpiperidin-2-yl]carbonyl}amino)pentanoyl]amino}pentyl]-1,3-thiazol-4-yl}carbonyl)amino]-2-methyl-5-phenylpentanoate 
• 1423117-90-1 C₂₅H₃₅N₃O₅S 
• 943218-34-6 4-({2-[1-acetoxy-3-(2-amino-3-methyl-pentanoylamino)-4-methyl-pentyl]-thiazole-4-carbonyl}-amino)-2-methyl-5-phenyl-pentanoic acid methyl ester 
• 1423040-41-8 C₃₇H₅₅N₅O₇S 

Relevant academic research and scientific papers

A Straightforward Approach towards Cyclic Photoactivatable Tubulysin Derivatives

The development of a new photolabile protecting group containing an additional allyl functionality allows the synthesis of cyclic photoactivatable natural products. Cyclization occurs between the allyl moiety in the protecting group and a second double bond in the target molecule by means of ring-closing metathesis. Cyclization should increase the metabolic stability towards proteases. On the other hand, the conformational change should cause diminished biological activity. As illustrated for tubulysin derivatives, cyclic and photoactivatable drug candidates can easily be obtained in only two steps from simple building blocks through Ugi reaction and ring-closing metathesis. The photolabile protecting group is introduced by means of the isocyanide component during the Ugi reaction.

Stereoselective total synthesis of tubulysin v

The total synthesis of tubulysin V was accomplished in 1.0% overall yield with linear 13 steps. Our synthetic strategy featured the following two reactions. One is zinc-mediated aza-Barbier reaction of (R)-N-tert- butanesulfinyl imine 8 with β-ester group functionalized allylic bromide 9 to afford the chiral homo-allylic amine (7); the other is to employ the methodology of aqueous indium-mediated aza-Barbier reaction previously developed by our group, giving the chiral homo-allylic amine 13 with high efficiency. The total synthesis of tubulysin V was accomplished in 1.0% overall yield with linear 13 steps. Our synthetic strategy featured the following two reactions. One is zinc-mediated aza-Barbier reaction of (R)-N-tert-butanesulfinyl imine 8 with β-ester group functionalized allylic bromide 9 to afford the chiral homo-allylic amine 7; the other is to employ the methodology of aqueous indium-mediated aza-Barbier reaction previously developed by our group, giving the chiral homo-allylic amine 13 with high efficiency. Copyright

Asymmetric syntheses of α-methyl γ-amino acid derivatives

This project was undertaken to demonstrate the potential of asymmetric hydrogenations mediated by the chiral, carbene-oxazoline analogue of Crabtree's catalyst "cat" in asymmetric hydrogenations of allylic amine derivatives of amino acids. Peripheral feat

Synthesis and biological evaluation of pretubulysin and derivatives

Pretubulysin, a biosynthetic precursor of the tubulysins, shows potent biological activity in the subnanomolar range towards various tumor cell lines. Its activity is only slightly less than those of the structurally more complex tubulysins. With a straig

Total synthesis of tubulysin U and V

Multicomponent method: Tubulysins are among the most potent cytotoxic agents known. Now the first total synthesis of some members has been achieved by utilizing a rapid three-component reaction for the synthesis of the unusual central thiazole amino acid