919518-59-5

Basic information

• Product Name: 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
• Synonyms: 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
• CAS NO: 919518-59-5
• Molecular Weight: 547.716
• Mol File: 919518-59-5.mol

Chemical Properties

• CAS DataBase Reference: 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(CAS DataBase Reference)
• NIST Chemistry Reference: 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(919518-59-5)
• EPA Substance Registry System: 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(919518-59-5)

Safety Data

• Hazardous Substances Data: 919518-59-5(Hazardous Substances Data)

Upstream product

• 368870-63-7 (3R,5R)-tert-butyl 5-benzyl-3-methyl-2-oxopyrrolidine-1-carboxylate 
• 368870-65-9 (2S,4R)-4-((tert-butoxycarbonyl)amino)-2-methyl-5-phenylpentanoic acid 
• 919518-49-3 2-{(1R,3R)-3-[(tert-butoxycarbonyl)amino]-1-hydroxy-4-methylpentyl}-1,3-thiazole-4-carboxylic acid 
• 852202-38-1 (R)-tert-butyl (2-methylhex-5-en-3-yl)carbamate 
• 1072804-64-8 (S)-2-methyl N-((R)-2-methylhex-5-en-3-yl)propane-2-sulfinamide 
• 24424-99-5 di-tert-butyl dicarbonate 
• 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 
• 124754-81-0 tert-butyl [(1R)-2-methyl-1-(2-oxoethyl)propyl]carbamate 
• 919518-38-0 methyl (2S,4R)-4-[(tert-butoxycarbonyl)amino]-2-methyl-5-phenylpentanoate 
• 919518-47-1 methyl 2-{(1R,3R)-1-acetoxy-3-[(tert-butoxycarbonyl)amino]-4-methylpentyl}-1,3-thiazole-4-carboxylate 
• 919518-36-8 methyl (2S,4R)-4-[(tert-butoxycarbonyl)(p-toluenesulfonyl)amino]-2-methyl-5-phenylpentanoate 

Downstream Products

• 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 
• 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 
• 1303556-54-8 C₃₄H₅₁N₅O₇S 
• 1303556-53-7 C₃₃H₅₁N₅O₆S 

Relevant articles and documents

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

Toward tubulysin: Gram-scale synthesis of tubuvaline-tubuphenylalanine fragment

(Chemical Equation Presented) A practical and stereoselective synthesis of the tubuvaline-tubuphenylalanine (Tuv-Tup) fragment of tubulysin is achieved involving the opening of aziridine, crucial MacMillan α-hydroxylation on both fragments, and an epoxide

Total synthesis of tubulysins U and V

Meeting the challenge: A reliable and modular reaction sequence has been developed for the synthesis of the challenging tubulysin framework. This route allows preparation of hundreds of milligrams of the stereochemically pure tetrapeptides (see picture), which are produced in small amounts by two different species of myxobacteria. Thus, full biological evaluation of the tubulysins and their analogues is now a real possibility. (Chemical Equation Presented).

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