74257-60-6

Basic information

• Product Name: (S)-tert-butyl 2-((S)-1-(benzyloxy)-1-oxo-3-phenylpropan-2-ylcarbamoyl)pyrrolidine-1-carboxylate
• Synonyms: (S)-tert-butyl 2-((S)-1-(benzyloxy)-1-oxo-3-phenylpropan-2-ylcarbamoyl)pyrrolidine-1-carboxylate
• CAS NO: 74257-60-6
• Molecular Weight: 452.55
• Mol File: 74257-60-6.mol
• Article Data: 9

Chemical Properties

• CAS DataBase Reference: (S)-tert-butyl 2-((S)-1-(benzyloxy)-1-oxo-3-phenylpropan-2-ylcarbamoyl)pyrrolidine-1-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-tert-butyl 2-((S)-1-(benzyloxy)-1-oxo-3-phenylpropan-2-ylcarbamoyl)pyrrolidine-1-carboxylate(74257-60-6)
• EPA Substance Registry System: (S)-tert-butyl 2-((S)-1-(benzyloxy)-1-oxo-3-phenylpropan-2-ylcarbamoyl)pyrrolidine-1-carboxylate(74257-60-6)

Safety Data

• Hazardous Substances Data: 74257-60-6(Hazardous Substances Data)

Upstream product

• 115655-70-4 (S) tert-butyl 2-(1H-imidazole-1-carbonyl)pyrrolidine-1-carboxylate 
• 1738-78-9 L-phenylalanine benzyl ester p-toluene-sulfonic acid salt 
• 3392-10-7 tert-butoxycarbonyl-L-proline N-hydroxysuccinimide ester 
• 15761-39-4 1-(tert-butoxycarbonyl)-L-proline 
• 2462-32-0 L-phenylalanine benzyl ester hydrochloride 
• 34101-07-0 (2S)-2-[N-(tert-butoxycarbonyl)amino]-1-imidazol-1-yl-3-phenylpropan-1-one 
• 66617-58-1 N-(tert-butoxycarbonyl)-L-phenylalanine benzyl ester 
• 52071-65-5 N-tert-butyloxycarbonyl-L-prolyl-L-phenylalanine 
• 962-39-0 L-Phenylalanine benzyl ester 
• 13734-34-4 N-tert-butoxycarbonyl-L-phenylalanine 

Downstream Products

• 5654-85-3 (3S,8aS)-3-benzyloctahydropyrrolo[1,2-a]pyrazine-1,4-dione 
• 126706-69-2 C₆₆H₈₀N₈O₁₀ 
• 126706-67-0 (S)-2-{[(S)-1-((S)-3-(1-Benzyl-1H-imidazol-4-yl)-2-{(2S,3S)-2-[(S)-3-(4-benzyloxy-phenyl)-2-tert-butoxycarbonylamino-propionylamino]-3-methyl-pentanoylamino}-propionyl)-pyrrolidine-2-carbonyl]-amino}-3-phenyl-propionic acid benzyl ester 
• 738550-99-7 (S)-2-({(S)-1-[(S)-2-{(2S,3S)-2-[(S)-2-((S)-2-Amino-3-methyl-butyrylamino)-3-(4-benzyloxy-phenyl)-propionylamino]-3-methyl-pentanoylamino}-3-(1-benzyl-1H-imidazol-4-yl)-propionyl]-pyrrolidine-2-carbonyl}-amino)-3-phenyl-propionic acid benzyl ester 
• 759423-68-2 (S)-2-({(S)-1-[(S)-2-{(2S,3S)-2-[(S)-2-Amino-3-(4-benzyloxy-phenyl)-propionylamino]-3-methyl-pentanoylamino}-3-(1-benzyl-1H-imidazol-4-yl)-propionyl]-pyrrolidine-2-carbonyl}-amino)-3-phenyl-propionic acid benzyl ester 
• 126706-65-8 (S)-2-({(S)-1-[(S)-3-(1-Benzyl-1H-imidazol-4-yl)-2-((2S,3S)-2-tert-butoxycarbonylamino-3-methyl-pentanoylamino)-propionyl]-pyrrolidine-2-carbonyl}-amino)-3-phenyl-propionic acid benzyl ester 
• 109068-26-0 (S)-2-({(S)-1-[(S)-2-((2S,3S)-2-Amino-3-methyl-pentanoylamino)-3-(1-benzyl-1H-imidazol-4-yl)-propionyl]-pyrrolidine-2-carbonyl}-amino)-3-phenyl-propionic acid benzyl ester 
• 78746-26-6 (S)-2-({(S)-1-[(S)-2-Amino-3-(1-benzyl-1H-imidazol-4-yl)-propionyl]-pyrrolidine-2-carbonyl}-amino)-3-phenyl-propionic acid benzyl ester 
• 357429-22-2 N-{N-[(2S)-1-(tert-butyldimethylsilyl)-4-oxoazetidine-2-carbonyl]-L-(benzyl)histidyl}-L-prolyl-L-phenylalanine benzyl ester 
• 357429-23-3 N-{N-[(2S)-4-oxoazetidine-2-carbonyl]-L-(benzyl)histidyl}-L-prolyl-L-phenylalanine benzyl ester 

Relevant articles and documents

Catalytic dehydrative peptide synthesis with gem-diboronic acids

Alkane-gem-diboronic acids have emerged as versatile organoboron catalysts for dehydrative amidation of α-Amino acids. A phenol-substituted multiboron catalyst with a B-C-B structure outperformed simple arylboronic acids in the condensation of α-Amino acids with suppressed epimerization of electrophiles. gem-diboronic acid catalysis were compatible with various O, N, and S-functionalized α-Amino acids bearing N-protecting groups including common carbamates used in peptide synthesis (Boc, Cbz, Fmoc). N-Trifluoroacetyl protection enabled an unprecedented catalytic dehydrative peptide synthesis at room temperature. Preliminary mechanistic studies revealed carboxylate-binding nature of gem-diboronic acids, orthogonal to the activation of carboxylic acids by arylboronic acids. The distinctive reactivity of the gem-diboronic acids would open prospects for mild catalytic peptide condensation.

Total Synthesis of Gombamide A

The first total synthesis of Gombamide A (1), a cytotoxic cyclic thiopeptide from the sponge Clathria gombawuiensis, has been achieved. Highlights of the convergent synthesis feature a disulfide bond forming cascade to close the 17-membered macrocycle and a selenoazidylation procedure to access the unusual para-hydroxystyrlyamide (pHSA) moiety. The synthesis required 18 steps, 11 steps in its longest linear sequence, and proceeded in 9.1% overall yield. This work will facilitate the study of the biological effects of Gombamide A and provide groundwork to explore the structure-activity relationship around this rare natural product.

Novel peptide isosteres that were designed to inhibit the binding of the HIV surface glycoprotein (gp120) to the T cell surface glycoprotein CD4

The cis- and trans-isomers of (2S)-2-[3′(RS)-3′-benzyl-3′-benzyloxycarbonylprop-1′- enyl]-N-methoxycarbonylcarbonylpyrrolidines have been prepared from a Wittig reaction between (S)-N-Boc-prolinal and the phosphorus ylide from (2RS)-3-iodo-2-benzyl-1-triisopropylsilyloxypropane. In addition, (2S)-N-methoxycarbonylcarbonyl-2-[(3′RS)-1-oxo-3′-benzyl-3′- benzyloxycarbonylpropyl]pyrrolidine was prepared from the cis-alkene produced in the Wittig reaction. These were intended as peptide isosteres of the known inhibitors of HIV-lymphocyte binding N-methoxycarbonylcarbonylprolylphenylalanyl benzyl esters, but did not possess such activity.