173204-72-3

Upstream product

• 37553-64-3 (S)-methyl 2-((tert-butoxycarbonyl)(methyl)amino)-3-phenylpropanoate 
• 51987-73-6 (S)-2-tert-butoxycarbonylamino-3-phenyl-propionic acid methyl ester 
• 169057-29-8 (R)-1-(oxiran-2-yl)-2-phenylethanone 
• 238753-81-6 Methyl-((S)-1-(S)-oxiranyl-2-phenyl-ethyl)-carbamic acid tert-butyl ester 
• 173204-71-2 tert-butyl (S)-N-methyl-N-(1-oxo-3-phenylpropan-2-yl)carbamate 
• 1730-25-2 allylmagnesium bromide 
• 238753-80-5 Methyl-((S)-1-(S)-oxiranyl-2-phenyl-ethyl)-amine 
• 24424-99-5 di-tert-butyl dicarbonate 

Downstream Products

• 238753-82-7 ((1S,2R)-1-Benzyl-2-methoxymethoxy-pent-4-enyl)-methyl-carbamic acid tert-butyl ester 
• 238753-83-8 [1-benzyl-2-(tert-butyl-dimethyl-silanyloxy)-pent-4-enyl]-methyl-carbamic acid tert-butyl ester 
• 159542-04-8 (-)-hapalosin 
• 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 
• 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 
• 173204-68-7 (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 
• 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 
• 173204-77-8 (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 
• 173204-79-0 (2S,5S,6R,10R,11S)-5-Benzyl-6-(tert-butyl-dimethyl-silanyloxy)-10-heptyl-2-isopropyl-4,11-dimethyl-1,9-dioxa-4-aza-cyclododecane-3,8,12-trione 
• 173204-69-8 (2S,3R)-2-Methylamino-1-phenyl-hex-5-en-3-ol 

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.

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.