173204-79-0

Upstream product

• 391871-69-5 (S)-2-(benzyloxy)-3-methylbutanoic acid 
• 110298-78-7 methyl (S)-2-(benzyloxy)-3-methylbutanoate 
• 173204-68-7 (2S,3R)-3-Hydroxy-2-methyl-decanoic acid (S)-1-{[(1S,2R)-1-benzyl-2-(tert-butyl-dimethyl-silanyloxy)-3-carboxy-propyl]-methyl-carbamoyl}-2-methyl-propyl ester 
• 716371-59-4 (3R,4S)-4-(N-((S)-2-benzyloxy-3-methylbutanoyl)-N-methylamino)-3-tert-butyldimethylsilyloxy-5-phenylpentanoic acid 
• 37553-64-3 (S)-methyl 2-((tert-butoxycarbonyl)(methyl)amino)-3-phenylpropanoate 
• 173204-76-7 (2S,3R)-3-(4-Methoxy-benzyloxy)-2-methyl-decanal 
• 173204-75-6 1-Methoxy-4-[(R)-1-((R)-1-methyl-allyl)-octyloxymethyl]-benzene 
• 173204-72-3 (2S,3R)-2-[N-(t-butyloxycarbonyl)-N-methylamino]-1-phenylhex-5-en-3-ol 
• 173204-69-8 (2S,3R)-2-Methylamino-1-phenyl-hex-5-en-3-ol 
• 173326-39-1 (3R,4R)-3-methylundec-1-en-4-ol 
• 173204-77-8 (2S,3R)-3-(4-Methoxy-benzyloxy)-2-methyl-decanoic acid (S)-1-{[(1S,2R)-1-benzyl-2-(tert-butyl-dimethyl-silanyloxy)-pent-4-enyl]-methyl-carbamoyl}-2-methyl-propyl ester 
• 173204-74-5 (2S,3R)-3-(4-Methoxy-benzyloxy)-2-methyl-decanoic acid (S)-1-[((1S,2R)-1-benzyl-2-hydroxy-pent-4-enyl)-methyl-carbamoyl]-2-methyl-propyl ester 
• 173204-78-9 (2S,3R)-3-Hydroxy-2-methyl-decanoic acid (S)-1-{[(1S,2R)-1-benzyl-2-(tert-butyl-dimethyl-silanyloxy)-4-oxo-butyl]-methyl-carbamoyl}-2-methyl-propyl ester 
• 173204-80-3 (2S,3R)-3-Hydroxy-2-methyl-decanoic acid (S)-1-{[(1S,2R)-1-benzyl-2-(tert-butyl-dimethyl-silanyloxy)-pent-4-enyl]-methyl-carbamoyl}-2-methyl-propyl ester 

Downstream Products

• 159542-04-8 (-)-hapalosin 

Relevant academic research and scientific papers

A practical total synthesis of hapalosin, a 12-membered cyclic depsipeptide with multidrug resistance-reversing activity, by employing improved segment coupling and macrolactonization

A practical total synthesis of hapalosin, a compound with multidrug resistance-reversing activity, has been carried out using an unprecedented macrolactonization strategy. One of the features of the new approach is the straightforward and fully stereocont

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.