178113-67-2

Upstream product

• 936226-69-6 (3R,4S)-4-tert-Butoxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)-5-phenyl-pentanoic acid ethyl ester 
• 178267-25-9 (3R,4S)-4-tert-Butoxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)-5-phenyl-pentanoic acid 
• 178113-53-6 (4S,5R)-3-((2S,3R)-3-hydroxy-2-methyl-1-oxodecanyl)-4-methyl-5-phenyl-2-oxazolidinone 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 72155-47-6 N-(tert-butoxycarbonyl)-4(S)-amino-3(R)-hydroxy-5-phenylpentanoic acid ethyl ester 
• 124-13-0 Octanal 
• 17407-55-5 (S)-2-Hydroxy-3-methylbutanoic acid 
• 238753-85-0 Acetic acid (R)-1-((R)-1-phenyl-ethyl)-octyl ester 
• 238753-86-1 (2S,3R)-3-Hydroxy-2-methyl-decanoic acid ethyl ester 
• 238753-84-9 (2R,3R)-2-Phenyl-decan-3-ol 
• 185208-61-1 (2S,3R)-3-[(3R,4S)-4-(tert-Butoxycarbonyl-methyl-amino)-3-(tert-butyl-dimethyl-silanyloxy)-5-phenyl-pentanoyloxy]-2-methyl-decanoic acid benzyl ester 
• 178113-66-1 (3R,4S)-4-(tert-Butoxycarbonyl-methyl-amino)-3-(tert-butyl-dimethyl-silanyloxy)-5-phenyl-pentanoic acid 
• 178113-54-7 benzyl (2S,3R)-3-hydroxy-2-methyldecanoate 
• 25047-67-0 n-heptyllithium 

Downstream Products

• 159542-04-8 (-)-hapalosin 
• 185208-63-3 (1R)-1-((1S)-2-{[(1S)-1-carboxy-2-methylpropyl]oxy}-1-methyl-2-oxoethyl)octyl 2,4,5-trideoxy-4-(methylamino)-5-phenyl-L-erythro-pentonate 
• 238753-91-8 (1R)-1-((1S)-2-{[(1S)-1-carboxy-2-methylpropyl]oxy}-1-methyl-2-oxoethyl)octyl 4-[(tert-butoxycarbonyl)(methyl)amino]-2,4,5-trideoxy-5-phenyl-L-erythro-pentonate 
• 185208-62-2 (2S,3R)-3-[(3R,4S)-4-(tert-Butoxycarbonyl-methyl-amino)-3-hydroxy-5-phenyl-pentanoyloxy]-2-methyl-decanoic acid (S)-1-allyloxycarbonyl-2-methyl-propyl ester 

Relevant academic research and scientific papers

Total synthesis of the multidrug-resistance reversing agent hapalosin

Hapalosin, a new reversing MDR agent, has been synthesized by macrolactamisation of a linear precursor 2 derived from the coupling of a β-hydroxy γ-aminoacid 3 and two hydroxy-esters 4 and 5. The aminoacid 3 was stereoselectively obtained by opening of an anti β-aminoepoxide while the 3-hydroxyacid 4 was prepared by condensation of a lithium compound with (R)-2-phenyl-propanal followed by oxidation of the phenyl group.

Synthetic study on hapalosin, a cyclic depsipeptide possessing multidrug resistance reversing activities

Hapalosin possessing a multidrug resistance reversing activity, has been synthesized from the corresponding hydroxy acids and γ-amino acids. The stereochemistry of the natural product and related derivatives is discussed.

Chemical study on hapalosin, a cyclic depsipeptide possessing multidrug resistance reversing activities: Synthesis, structure and biological activity

Hapalosin 1 possessing a multidrug resistance reversing activity, has been synthesized from the corresponding hydroxy acids A, C and γ-amino acid B. The stereochemistry of the natural product 1 and N-demethylhapalosin 11 is discussed by means of spectroscopic manner as well as molecular modeling studies. Biological evaluation of 1 and 11 indicated that a cis-amide function is a crucial factor for the MDR reversing activity.