178113-60-5

Upstream product

• 65138-05-8 (S)-2-hydroxy-3-methylbutyric acid benzyl ester 
• 178113-57-0 (4S,5R)-5-{(R)-1-[(S)-1-((S)-1-Allyloxycarbonyl-2-methyl-propoxycarbonyl)-ethyl]-octyloxycarbonylmethyl}-4-benzyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester 
• 178113-55-8 (4S,5R)-4-Benzyl-5-[(R)-1-((S)-1-benzyloxycarbonyl-ethyl)-octyloxycarbonylmethyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester 
• 178113-58-1 (4S,5R)-4-Benzyl-5-{(R)-1-[(S)-1-((S)-1-carboxy-2-methyl-propoxycarbonyl)-ethyl]-octyloxycarbonylmethyl}-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester 
• 178113-53-6 (4S,5R)-3-((2S,3R)-3-hydroxy-2-methyl-1-oxodecanyl)-4-methyl-5-phenyl-2-oxazolidinone 
• 178113-54-7 benzyl (2S,3R)-3-hydroxy-2-methyldecanoate 
• 178113-56-9 L-2-hydroxy-3-methylbutanoic acid allyl ester 
• 158895-85-3 4(S)-Benzyl-3-(tert-butoxycarbonyl)-2,2-dimethyl-5(R)-oxazolidineacetic acid 
• 181715-10-6 (3R,4S)-4-Benzyloxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)-5-phenyl-pentanoic acid (R)-1-((R)-1-methyl-allyl)-octyl ester 
• 181715-06-0 (2S,3R)-3-[(3R,4S)-4-Benzyloxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)-5-phenyl-pentanoyloxy]-2-methyl-decanoic acid (S)-1-benzyloxycarbonyl-2-methyl-propyl ester 
• 181715-13-9 (2S,3R)-3-[(3R,4S)-4-Benzyloxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)-5-phenyl-pentanoyloxy]-2-methyl-decanoic acid 
• 181715-12-8 (3R,4S)-4-Benzyloxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)-5-phenyl-pentanoic acid (R)-1-((S)-1-methyl-2-oxo-ethyl)-octyl ester 
• 181715-07-1 (S)-4-Benzyloxycarbonylamino-3-oxo-5-phenyl-pentanoic acid (R)-1-((R)-1-methyl-allyl)-octyl ester 
• 181715-09-3 (1R,2R)-1-n-heptyl-2-methyl-3-butenyl acetate 

Downstream Products

• 178113-59-2 N-desmethylhapalosin 

Relevant academic research and scientific papers

Synthesis and conformational analysis of the multidrug resistance-reversing agent hapalosin and its non-N-methyl analog

Hapalosin was initially synthesized by macrolactonization, and a second synthesis was achieved by cycloamidation. In both syntheses, three of the five stereocenters in hapalosin were established by two Brown allylboration reactions. The synthesis of the non-N-Me analog of hapalosin involved chelation-controlled reduction of a γ-amino-β-keto ester and cycloamidation. In CDCl3 at 25°C, synthetic hapalosin exists as a 2.3:1 mixture of conformers, while its non-N-Me analog exists only as a single conformer. 1H,1H-NOESY and computation reveal that the configuration of the amide bond is responsible for the conformations of the two compounds. The major conformer of hapalosin is found to be an s-cis amide, the minor conformer an s-trans amide, and the non-N-Me analog an s-trans amide. Applying distance constraints to protons that exhibit NOESY correlations, computation shows that the major conformer of hapalosin and the non-N-Me analog have very different conformations. By contrast, the minor conformer of hapalosin and the non-N-Me analog have very similar conformations.

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.