238753-90-7

Upstream product

• 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 
• 99113-30-1 ((1S,2R)-1-benzyl-2-hydroxybut-3-enyl)carbamic acid tert-butyl ester 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 159429-88-6 Methyl (2S,3R)-3-hydroxy-2-methyldecanoate 
• 178113-54-7 benzyl (2S,3R)-3-hydroxy-2-methyldecanoate 
• 178113-66-1 (3R,4S)-4-(tert-Butoxycarbonyl-methyl-amino)-3-(tert-butyl-dimethyl-silanyloxy)-5-phenyl-pentanoic acid 
• 229981-28-6 (3R,4S)-N-(tert-butoxycarbonyl)-4-amino-3-(tert-butyldimethylsilyloxy)-5-phenylpent-1-ene 
• 261785-50-6 (2S,3R)-3-hydroxy-2-methyl-4-pentenoic acid methyl ester 
• 461696-66-2 (3R,4R)-O-acetyl-4-[N-(tert-butoxycarbonyl)amino]-5-phenylpent-1-en-3-ol 
• 156048-63-4 Acetic acid (R)-1-((S)-1-tert-butoxycarbonylamino-2-phenyl-ethyl)-allyl ester 
• 72155-47-6 N-(tert-butoxycarbonyl)-4(S)-amino-3(R)-hydroxy-5-phenylpentanoic acid ethyl ester 
• 178113-53-6 (4S,5R)-3-((2S,3R)-3-hydroxy-2-methyl-1-oxodecanyl)-4-methyl-5-phenyl-2-oxazolidinone 
• 178267-25-9 (3R,4S)-4-tert-Butoxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)-5-phenyl-pentanoic acid 
• 936226-69-6 (3R,4S)-4-tert-Butoxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)-5-phenyl-pentanoic acid ethyl ester 

Downstream Products

• 159542-04-8 (-)-hapalosin 
• 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 
• 314030-97-2 (1R)-1-[(1S)-2-({(1S)-1-[(benzyloxy)carbonyl]-2-methylpropyl}oxy)-1-methyl-2-oxoethyl]octyl 4-[(tert-butoxycarbonyl)(methyl)amino]-2,4,5-trideoxy-5-phenyl-L-erythro-pentonate 
• 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 
• 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

Synthesis and biological activities of hapalosin derivatives with modification at the C12 position

Among the hapalosin derivatives synthesized, the compounds carrying methyl (5a), methylthioethyl (5d) and phenylmethyl (5e) groups at the C12 position possess only the cis-peptide structure, in contrast to the cases of 5b and 5c. In addition to their conformational stability, the biological activities of the compounds were determined in relation of the P- glycoprotein-mediated MDR-reversing activity and induction of apoptosis.

A stereocontrolled synthesis of hapalosin

A facile synthetic method for two components of hapalosin, that is, β-hydroxy-γ-amino acid and β-hydroxy acid, has been established by utilizing chiral building blocks efficiently resolved in a lipase-catalyzed transesterification. Furthermore, the synthe

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.

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.

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.