83487-17-6

Upstream product

• 40216-83-9 L-4-hydroxyproline methyl ester hydrochloride 
• 79-22-1 methyl chloroformate 

Downstream Products

• 176747-44-7 (2S,4R)-4-hydroxy-α,α-diphenyl-2-pyrrolidinemethanol 
• 845965-30-2 (6R,7aS)-6-Hydroxy-1,1-diphenyl-tetrahydro-pyrrolo[1,2-c]oxazol-3-one 
• 1185745-38-3 (3R,5S)-5-(bis(3,5-bis(trifluoromethyl)phenyl)(hydroxy)methyl)pyrrolidin-3-ol 
• 1360588-94-8 (6R,7aS)-1,1-bis[3,5-bis(trifluoromethyl)phenyl]-6-hydroxytetrahydropyrrolo[1,2-c]oxazol-3(1H)-one 
• 1498288-80-4 (2S,4S)-2-[bis[3,5-bis(trifluoromethyl)phenyl]hydroxymethyl]-4-(dimethylamino)pyrrolidine 
• 1498288-75-7 (6S,7aS)-6-amino-1,1-bis[3,5-bis(trifluoromethyl)phenyl]tetrahydropyrrolo[1,2-c]oxazol-3(1H)-one 
• 1498288-73-5 (6R,7aS)-1,1-bis[3,5-bis(trifluoromethyl)phenyl]-3-oxohexahydropyrrolo[1,2-c]oxazol-6-yl methanesulfonate 
• 1498288-99-5 (2S,4R)-2-[bis[3,5-bis(trifluoromethyl)phenyl]hydroxymethyl]-4-(dimethylamino)pyrrolidine 
• 1498288-93-9 C₂₉H₁₆F₁₂N₂O₆ 
• 1498288-98-4 (6R,7aS)-1,1-bis[3,5-bis(trifluoromethyl)phenyl]-6-(dimetylamino)tetrahydropyrrolo[1,2-c]oxazol-3(1H)-one 
• 1498288-96-2 (6R,7aS)-6-azido-1,1-bis[3,5-bis(trifluoromethyl)phenyl]-tetrahydropyrrolo[1,2-c]oxazol-3(1H)-one 
• 1498288-94-0 (6S,7aS)-1,1-bis[3,5-bis(trifluoromethyl)phenyl]-6-hydroxytetrahydropyrrolo[1,2-c]oxazol-3(1H)-one 
• 1498288-92-8 C₄₃H₆₂F₁₂N₂OSi 
• 1498288-91-7 C₃₉H₅₄F₁₂N₂OSi 

Relevant academic research and scientific papers

Domino Process Achieves Site-Selective Peptide Modification with High Optical Purity. Applications to Chain Diversification and Peptide Ligation

The development of peptide libraries by site-selective modification of a few parent peptides would save valuable time and materials in discovery processes but still is a difficult synthetic challenge. Herein, we introduce natural hydroxyproline as a convertible unit for the production of a variety of optically pure amino acids, including expensive N-alkyl amino acids, homoserine lactones, and Agl lactams, and to achieve the mild, efficient, and site-selective modification of peptides. A domino process is used to cleave the customizable Hyp unit under mild, metal-free conditions. Both terminal and internal positions can be modified, and similar customizable units can be differentiated. The resulting products possess two reactive chains which can be manipulated independently. The versatility and scope of this process is highlighted by its application to the ligation of two peptide chains, and the generation of peptides with several chains and peptides with conformational restrictions.

A formal synthesis of (+)-lactacystin from 4-hydroxyproline

A formal synthesis of (+)-lactacystin has been completed from trans-4-hydroxyproline, using a diastereoselective enolate acylation reaction as a key step. Diastereoselectivity was seen to vary as a function of the steric bulk of the C4-O-protecting group, and contrary to expectations, the best diastereoselectivities were obtained when the small methyl carbonate protecting group was used. The formal synthesis was then completed by intercepting Shibasaki's route via methyl carbonate deprotection, dehydration, 3-pyrroline to 3-pyrrolinone oxidation, hydrogenation and N-CO2Me deprotection.

4'-Methyloxycarbamyl-3'-deoxy-5-methyluridine; synthesis of a novel nucleoside analogue

The preparation of 4'-methyloxycarbamyl-3'-deoxythymidine from chiral amino acid precursors is described. The route chosen employs a hitherto unreported electrochemical oxidation of a suitably protected derivative of trans-4-hydroxy-L-proline, to obtain the key intermediate compound. Conventional condensation methodology is then used to arrive at the target nucleoside.

Electrochemical Oxidation of Proline Derivatives: Total Syntheses of Bulgecinine and Bulgecin C

The influence of structure on the efficiency of the electrochemical C-5 oxidation of (2S,4S)-hydroxyproline carbamate esters is presented.Optimum methoxylation was observed with (2S,4S)-4-acetoxy-1,2-pyrrolidine-dicarboxylic acid 2-methyl 1-(2-(trimethylsilyl)ethyl) ester (19).The corresponding C-5 methoxy derivative 20 was converted into bulgecinine (4) via a stereospecific radical homologation to incorporate the C-5 hydroxymethyl substituent.Bulgecin C (1c) was prepared via a β-stereoselective glycosidation reaction using a 2-azido-2-deoxy-α-D-glucopyranosyl trichloroacetimidate derivative, regiospecific C-4' sulfation, and deprotection.