541511-47-1

Basic information

• Product Name: (E)-(2R,3R)-3-Hydroxy-2,4-dimethyl-hept-4-enoic acid methoxy-methyl-amide
• Synonyms: (E)-(2R,3R)-3-Hydroxy-2,4-dimethyl-hept-4-enoic acid methoxy-methyl-amide
• CAS NO: 541511-47-1
• Molecular Weight: 215.293
• Mol File: 541511-47-1.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (E)-(2R,3R)-3-Hydroxy-2,4-dimethyl-hept-4-enoic acid methoxy-methyl-amide(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-(2R,3R)-3-Hydroxy-2,4-dimethyl-hept-4-enoic acid methoxy-methyl-amide(541511-47-1)
• EPA Substance Registry System: (E)-(2R,3R)-3-Hydroxy-2,4-dimethyl-hept-4-enoic acid methoxy-methyl-amide(541511-47-1)

Safety Data

• Hazardous Substances Data: 541511-47-1(Hazardous Substances Data)

Upstream product

• 6638-79-5 N,O-dimethylhydroxylamine*hydrochloride 
• 779353-80-9 (4R,5S)-3-((E)-(2R,3R)-3-Hydroxy-2,4-dimethyl-hept-4-enoyl)-4-methyl-5-phenyl-oxazolidin-2-one 

Relevant articles and documents

Aurilide, a cytotoxic depsipeptide from the sea hare Dolabella auricularia: Isolation, structure determination, synthesis, and biological activity

The bioassay-guided fractionation of the cytotoxic constituents of the Japanese sea hare Dollabella auricularia led to the isolation of aurilide (1), a 26-membered cyclodepsipeptide. The gross structure of 1 was established by spectroscopic analysis including 2D NMR techniques. The absolute stereostructure was determined by chiral HPLC analysis of acid hydrolysates of 1 and by the enantioselective synthesis of a degradation product arising from a dihydroxylated fatty acid portion. The enantioselective synthesis of 1 was achieved in 12% overall yield (16 steps) and confirmed the absolute stereostructure of 1. The cytotoxicity of 1 was evaluated using a synthetic sample, which was found to exhibit potent cytotoxicity against HeLa S 3 cells with an IC50 of 0.011 μg/mL. Further biological and pharmacological studies of 1 have been carried out by using synthetic 1. Graphical abstract.