181715-07-1

Basic information

• Product Name: (S)-4-Benzyloxycarbonylamino-3-oxo-5-phenyl-pentanoic acid (R)-1-((R)-1-methyl-allyl)-octyl ester
• Synonyms: (S)-4-Benzyloxycarbonylamino-3-oxo-5-phenyl-pentanoic acid (R)-1-((R)-1-methyl-allyl)-octyl ester
• CAS NO: 181715-07-1
• Molecular Weight: 507.67
• Mol File: 181715-07-1.mol

Chemical Properties

• CAS DataBase Reference: (S)-4-Benzyloxycarbonylamino-3-oxo-5-phenyl-pentanoic acid (R)-1-((R)-1-methyl-allyl)-octyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-4-Benzyloxycarbonylamino-3-oxo-5-phenyl-pentanoic acid (R)-1-((R)-1-methyl-allyl)-octyl ester(181715-07-1)
• EPA Substance Registry System: (S)-4-Benzyloxycarbonylamino-3-oxo-5-phenyl-pentanoic acid (R)-1-((R)-1-methyl-allyl)-octyl ester(181715-07-1)

Safety Data

• Hazardous Substances Data: 181715-07-1(Hazardous Substances Data)

Upstream product

• 173326-39-1 (3R,4R)-3-methylundec-1-en-4-ol 
• 124-13-0 Octanal 
• 1161-13-3 N-Cbz-L-Phe 
• 181715-09-3 (1R,2R)-1-n-heptyl-2-methyl-3-butenyl acetate 

Downstream Products

• 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 
• 178113-60-5 (2S,5S,6R,10R,11S)-5-Benzyl-6-(tert-butyl-dimethyl-silanyloxy)-10-heptyl-2-isopropyl-11-methyl-1,9-dioxa-4-aza-cyclododecane-3,8,12-trione 
• 178113-59-2 N-desmethylhapalosin 

Relevant articles and documents

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.