203053-99-0

Basic information

• Product Name: (S)-1-[(1S,2R,3S,4R)-3-({(S)-1-[(S)-2-((S)-2-Benzyloxycarbonylamino-4-methyl-pentanoylamino)-propionyl]-pyrrolidine-2-carbonyl}-amino)-bicyclo[2.2.1]hept-5-ene-2-carbonyl]-pyrrolidine-2-carboxylic acid tert-butyl ester
• Synonyms: (S)-1-[(1S,2R,3S,4R)-3-({(S)-1-[(S)-2-((S)-2-Benzyloxycarbonylamino-4-methyl-pentanoylamino)-propionyl]-pyrrolidine-2-carbonyl}-amino)-bicyclo[2.2.1]hept-5-ene-2-carbonyl]-pyrrolidine-2-carboxylic acid tert-butyl ester
• CAS NO: 203053-99-0
• Molecular Weight: 721.894
• Mol File: 203053-99-0.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (S)-1-[(1S,2R,3S,4R)-3-({(S)-1-[(S)-2-((S)-2-Benzyloxycarbonylamino-4-methyl-pentanoylamino)-propionyl]-pyrrolidine-2-carbonyl}-amino)-bicyclo[2.2.1]hept-5-ene-2-carbonyl]-pyrrolidine-2-carboxylic acid tert-butyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-1-[(1S,2R,3S,4R)-3-({(S)-1-[(S)-2-((S)-2-Benzyloxycarbonylamino-4-methyl-pentanoylamino)-propionyl]-pyrrolidine-2-carbonyl}-amino)-bicyclo[2.2.1]hept-5-ene-2-carbonyl]-pyrrolidine-2-carboxylic acid tert-butyl ester(203053-99-0)
• EPA Substance Registry System: (S)-1-[(1S,2R,3S,4R)-3-({(S)-1-[(S)-2-((S)-2-Benzyloxycarbonylamino-4-methyl-pentanoylamino)-propionyl]-pyrrolidine-2-carbonyl}-amino)-bicyclo[2.2.1]hept-5-ene-2-carbonyl]-pyrrolidine-2-carboxylic acid tert-butyl ester(203053-99-0)

Safety Data

• Hazardous Substances Data: 203053-99-0(Hazardous Substances Data)

Upstream product

• 203053-79-6 (S)-1-[(S)-2-((S)-2-Benzyloxycarbonylamino-4-methyl-pentanoylamino)-propionyl]-pyrrolidine-2-carboxylic acid 2-trimethylsilanyl-ethyl ester 
• 187087-44-1 (S)-1-((1S,2R,3S,4R)-3-Carboxy-bicyclo[2.2.1]hept-5-ene-2-carbonyl)-pyrrolidine-2-carboxylic acid tert-butyl ester 
• 187087-48-5 (S)-1-((1S,2R,3S,4R)-3-Azidocarbonyl-bicyclo[2.2.1]hept-5-ene-2-carbonyl)-pyrrolidine-2-carboxylic acid tert-butyl ester 
• 108827-49-2 H-Pro-OTmse 
• 2812-46-6 proline tert-butyl ester 
• 2817-13-2 ((S)-2-(benzyloxycarbonylamino)-4-methylpentanamido)propanoic acid 
• 187087-50-9 (S)-1-((1S,2R,3S,4R)-3-Isocyanato-bicyclo[2.2.1]hept-5-ene-2-carbonyl)-pyrrolidine-2-carboxylic acid tert-butyl ester 
• 203053-76-3 (S)-1-[(S)-2-((S)-2-Benzyloxycarbonylamino-4-methyl-pentanoylamino)-propionyl]-pyrrolidine-2-carboxylic acid 

Downstream Products

• 203054-01-7 (S)-1-[(1S,2R,3S,4R)-3-({(S)-1-[(S)-2-((S)-2-Benzyloxycarbonylamino-4-methyl-pentanoylamino)-propionyl]-pyrrolidine-2-carbonyl}-amino)-bicyclo[2.2.1]hept-5-ene-2-carbonyl]-pyrrolidine-2-carboxylic acid 

Relevant articles and documents

Synthesis of Peptides and Pseudopeptides Incorporating an endo-(2S,3R)-Norborn-5-ene Residue as a Turn Inducer

The desymmetrization of endo-norborn-5-ene-2,3-dicarboxylic anhydride (5) by proline derivatives is used to prepare peptides and pseudopeptides incorporating an endo-(2S,3R)-2-amino-3-carboxynorborn-5-ene (1) residue. The peptides contain a single conformationally constrained β-amino acid residue, while the pseudopeptides also contain a urea linkage and two peptide chains running in parallel directions. The key step in the synthesis is a Curtius rearrangement on the amido acids 6a,b to generate an isocyanate that is then directly reacted with suitably protected amino acids and peptides to give the peptides and pseudopeptides. The synthesis of the peptide analogue 4 is also described; in this compound, the two peptide chains run parallel to one another, and the stereochemistry of the norbornene unit within compound 4 was determined by X-ray analysis of the related peptide analogue 23.