240428-49-3

Basic information

• Product Name: N-<(1,1-dimethylethoxy)carbonyl>-2,2-dimethyl-β-alanyl-(2S)-2-hydroxy-4-(methylpentanoyl)-(2E,5S,6R,7E)-5-hydroxy-6-methyl-8-phenyl-2,7-octadienoyl-D-valine
• Synonyms: N-<(1,1-dimethylethoxy)carbonyl>-2,2-dimethyl-β-alanyl-(2S)-2-hydroxy-4-(methylpentanoyl)-(2E,5S,6R,7E)-5-hydroxy-6-methyl-8-phenyl-2,7-octadienoyl-D-valine
• CAS NO: 240428-49-3
• Molecular Weight: 658.833
• Mol File: 240428-49-3.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: N-<(1,1-dimethylethoxy)carbonyl>-2,2-dimethyl-β-alanyl-(2S)-2-hydroxy-4-(methylpentanoyl)-(2E,5S,6R,7E)-5-hydroxy-6-methyl-8-phenyl-2,7-octadienoyl-D-valine(CAS DataBase Reference)
• NIST Chemistry Reference: N-<(1,1-dimethylethoxy)carbonyl>-2,2-dimethyl-β-alanyl-(2S)-2-hydroxy-4-(methylpentanoyl)-(2E,5S,6R,7E)-5-hydroxy-6-methyl-8-phenyl-2,7-octadienoyl-D-valine(240428-49-3)
• EPA Substance Registry System: N-<(1,1-dimethylethoxy)carbonyl>-2,2-dimethyl-β-alanyl-(2S)-2-hydroxy-4-(methylpentanoyl)-(2E,5S,6R,7E)-5-hydroxy-6-methyl-8-phenyl-2,7-octadienoyl-D-valine(240428-49-3)

Safety Data

• Hazardous Substances Data: 240428-49-3(Hazardous Substances Data)

Upstream product

• 188346-49-8 1-<<(5S)-<<(1,1,-dimethylethyl)dimethylsilyl>oxy>-(6R)-methyl-1-oxo-8-phenyl-(2E,7E)-octadienyl>oxy>-2,5-pyrrolidinedione 
• 188346-50-1 1-<<(5S)-hydroxy-(6R)-methyl-1-oxo-8-phenyl-(2E,7E)-octadienyl>oxy>-2,5-pyrrolidinedione 
• 162465-28-3 (5S)-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-(6R)-methyl-8-phenyl-(2E,7E)-octadienoic acid methyl ester 
• 162465-29-4 (5S)-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-(6R)-methyl-8-phenyl-(2E,7E)-octadienoic acid 
• 640-68-6 D-Val-OH 
• 188346-51-2 (1S,3E)-5-<(2,5-dioxo-1-pyrrolidinyl)oxy>-1-<(1R,2E)-1-methyl-3-phenyl-2-propenyl>-5-oxo-3-pentenyl-(2S)-<3-<<(1,1-dimethylethoxy)carbonyl>amino>-2,2-dimethyl-1-oxopropoxy>-4-methylpentanoate 

Downstream Products

• 240428-67-5 cyclo<2,2-dimethyl-β-alanyl-(2S)-2-hydroxy-4-(methylpentanoyl)-(2E,5S,6R,7E)-5-hydroxy-6-methyl-8-phenyl-2,7-octadienoyl-D-valyl> 

Relevant articles and documents

Novel cryptophycin antitumor agents: Synthesis and cytotoxicity of fragment 'B' analogues

A general synthetic approach to novel cryptophycin analogues 6 is described. N-Hydroxysuccinimide active ester 15, a key common intermediate, was converted to β-epoxide 6 in three steps, via initial coupling with unprotected amino acid 9, followed by deprotection/macrolactamization of acyclic precursor 16, and final oxidation of styrene 7 to install the C7-C8 β-epoxide. Cryptophycin styrenes 7 and β-epoxides 6, bearing diverse side chains in fragment 'B', were evaluated for cytotoxic activity, β-Epoxides 6, in general, were significantly more potent than the corresponding α-epoxides 17 and styrenes 7. A benzyl side chain was required for potent activity, with β-epoxide 6u, possessing a 3-Cl,4-(dimethylamino)benzyl moiety, as the most potent cytotoxic agent prepared, with an IC50 = 54 pM, only 2-fold-less than that of Cryptophycin-52 (3).