88036-14-0

Upstream product

• 2130-97-4 (S)-N^α-phthaloyl-O-benzyltyrosine 

Downstream Products

• 88036-15-1 2-<5-<4-(benzyloxy)phenyl>-3-oxo-4(S)-phthalimidopentyl>-1,3-dioxolane 
• 251983-08-1 [(S)-3-(4-Benzyloxy-phenyl)-2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-propionyl]-phosphonic acid diethyl ester 
• 88036-25-3 8(S)-amino-4,7-dioxo-9-(4-hydroxyphenyl)nonanoyl-L-phenylalanyl-L-leucine 
• 88036-21-9 5-<2-<2-<4-(benzyloxy)phenyl>-1(S)-<<(2,2,2-trichloroethyloxy)carbonyl>amino>ethyl>-1,3-dioxolan-2-yl>-3-oxopentanoyl-L-phenylalanyl-L-leucine methyl ester 
• 88036-22-0 5-<2-<2-<4-(benzyloxy)phenyl>-1(S)-<<(2,2,2-trichloroethoxy)carbonyl>amino>ethyl>-1,3-dioxolan-2-yl>-3-oxopentanoyl-L-phenylalanyl-L-leucine 
• 88036-23-1 5-<2-<2-(4-hydroxyphenyl)-1(S)-<<(2,2,2-trichloroethoxy)carbonyl>amino>ethyl>-1,3-dioxolan-2-yl>-3-oxopentanoyl-L-phenylalanyl-L-leucine 
• 88036-24-2 4,7-dioxo-9-(4-hydroxyphenyl)-8(S)-<<(2,2,2-trichloroethoxy)carbonyl>amino>nonanoyl-L-phenylalanyl-L-leucine 
• 88036-18-4 2-<2-<4-(benzyloxy)phenyl>-1(S)-phthalimidoethyl>-2-<5-(1,3-dioxolan-2-yl)-3-hydroxypentyl>-1,3-dioxolane 
• 88036-20-8 2-<2-<4-(benzyloxy)phenyl>-1(S)-<<(2,2,2-trichloroethoxy)carbonyl>amino>ethyl>-2-(5-carboxy-5-oxopentyl)-1,3-dioxolane 
• 88036-16-2 2-<2-<4-(benzyloxy)phenyl>-1(S)-phthalimidoethyl>-2-<2-(1,3-dioxolan-2-yl)ethyl>-1,3-dioxolane 
• 88036-19-5 2-<1(S)-amino-2-<4-(benzyloxy)phenyl>ethyl>-2-<5-(1,3-dioxolan-2-yl)-3-hydroxypentyl>-1,3-dioxolane 
• 88036-17-3 2-<2-<4-(benzyloxy)phenyl>-1(S)-phthalimidoethyl>-2-(3-oxopropyl)-1,3-dioxolane 
• 306775-45-1 (S)-N^α-phthaloyl-O-benzyltyrosinylglycine 
• 306775-46-2 3-[2(S)-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-3-(4-benzyloxyphenyl)propanoyl]-1,3-oxazolidin-5-one 

Relevant academic research and scientific papers

Efficient synthesis of (S)-4-phthalimido-1,3,4,5-tetrahydro-8-(2,6-dichlorobenzyloxy)-3-oxo-2H-2-ben zazepin-2-acetic acid (Pht-Hba(2,6,Cl2-Bn)-Gly-OH)

4-Amino-2-benzazepin-3-ones have proven very useful for studying the biologically active conformations of peptides. The synthesis of Pht-Aba-Xaa-OH by reaction of the corresponding 1,3-oxazolidin-5-one with trifluoromethanesulfonic acid (TFMSA) has been reported in the literature. However, when this procedure was applied to the preparation of Pht-Hba(Bn)-Gly-OH 8, many byproducts were formed and the yield of the desired aminobenzazepinones 7 and 8 was very low. We report in this paper an efficient methodology for the synthesis of Pht-Hba(2,6-Cl2-Bn)-Gly-OH 17 starting from the commercially available tyrosine. In our procedure, the dipeptide Pht-Tyr(2,6-Cl2-Bn)-Gly-OH 15 is converted to the 1,3-oxazolidin-5-one 16 which then undergoes Friedel-Crafts cyclization in the presence of tin tetrachloride to afford the desired 4-phthalimido-1,3,4,5-tetrahydro-8-(2,6-dichlorobenzyloxy)-2-benzazepin-3-one 17 in excellent yield.

Replacement of the peptide-backbone amides connecting Tyr-Gly and Gly-Gly in leucine-enkephalin with ketomethylene groups: Synthesis and biological activity

A peptide analogue of Leu-enkephalin was synthesized in which the amide linkages between Tyr-Gly and Gly-Gly were replaced by ketomethylene groups. The resulting analogue, x, had 1/4000th and 1/2400th the opiate receptor binding activity of Leu-enkephalin