183794-64-1

Basic information

• Product Name: (S)-2-{(2S,6R,7S,9S)-2-(4-Benzyloxy-benzyl)-10-oxo-9-[3-(2-oxo-4,5-diphenyl-oxazol-3-yl)-propyl]-4-oxa-1,8-diaza-bicyclo[5.3.1]undec-6-ylamino}-3-(1H-indol-3-yl)-propionic acid
• Synonyms: (S)-2-{(2S,6R,7S,9S)-2-(4-Benzyloxy-benzyl)-10-oxo-9-[3-(2-oxo-4,5-diphenyl-oxazol-3-yl)-propyl]-4-oxa-1,8-diaza-bicyclo[5.3.1]undec-6-ylamino}-3-(1H-indol-3-yl)-propionic acid
• CAS NO: 183794-64-1
• Molecular Weight: 845.995
• Mol File: 183794-64-1.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (S)-2-{(2S,6R,7S,9S)-2-(4-Benzyloxy-benzyl)-10-oxo-9-[3-(2-oxo-4,5-diphenyl-oxazol-3-yl)-propyl]-4-oxa-1,8-diaza-bicyclo[5.3.1]undec-6-ylamino}-3-(1H-indol-3-yl)-propionic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-2-{(2S,6R,7S,9S)-2-(4-Benzyloxy-benzyl)-10-oxo-9-[3-(2-oxo-4,5-diphenyl-oxazol-3-yl)-propyl]-4-oxa-1,8-diaza-bicyclo[5.3.1]undec-6-ylamino}-3-(1H-indol-3-yl)-propionic acid(183794-64-1)
• EPA Substance Registry System: (S)-2-{(2S,6R,7S,9S)-2-(4-Benzyloxy-benzyl)-10-oxo-9-[3-(2-oxo-4,5-diphenyl-oxazol-3-yl)-propyl]-4-oxa-1,8-diaza-bicyclo[5.3.1]undec-6-ylamino}-3-(1H-indol-3-yl)-propionic acid(183794-64-1)

Safety Data

• Hazardous Substances Data: 183794-64-1(Hazardous Substances Data)

Upstream product

• 183794-62-9 (S)-2-{(2S,6R,7S,9S)-2-(4-Benzyloxy-benzyl)-10-oxo-9-[3-(2-oxo-4,5-diphenyl-oxazol-3-yl)-propyl]-4-oxa-1,8-diaza-bicyclo[5.3.1]undec-6-ylamino}-3-(1H-indol-3-yl)-propionic acid methyl ester 
• 21240-34-6 4,5-diphenyl-1,3-dioxol-2-one 
• 7524-52-9 (S)-tryptophan methyl ester hydrochloride 
• 21887-64-9 N₂-(tert-butoxycarbonyl)-L-ornithine 
• 183794-28-7 {(2R,3S)-3-[(S)-2-Amino-3-(4-benzyloxy-phenyl)-propoxymethyl]-oxiranyl}-methanol 
• 183794-29-8 (S)-1-[(3R,5S)-5-(4-Benzyloxy-benzyl)-morpholin-3-yl]-ethane-1,2-diol 
• 183794-32-3 (2S,6R,7R)-2-(4-Benzyloxy-benzyl)-7-(tert-butyl-dimethyl-silanyloxy)-4-oxa-1-aza-bicyclo[4.2.0]octane 
• 183794-30-1 Methanesulfonic acid (S)-2-[(3R,5S)-5-(4-benzyloxy-benzyl)-morpholin-3-yl]-2-hydroxy-ethyl ester 
• 183794-33-4 (S)-2-Amino-5-(2-oxo-4,5-diphenyl-oxazol-3-yl)-pentanoic acid methyl ester 
• 183794-31-2 Methanesulfonic acid (S)-2-[(3R,5S)-5-(4-benzyloxy-benzyl)-morpholin-3-yl]-2-(tert-butyl-dimethyl-silanyloxy)-ethyl ester 
• 183794-36-7 (S)-5-(2-Oxo-4,5-diphenyl-oxazol-3-yl)-2-(2-trimethylsilanyl-ethanesulfonylamino)-pentanoic acid 
• 183794-35-6 (S)-5-(2-Oxo-4,5-diphenyl-oxazol-3-yl)-2-(2-trimethylsilanyl-ethanesulfonylamino)-pentanoic acid methyl ester 
• 183794-26-5 [(S)-2-(4-Benzyloxy-phenyl)-1-((Z)-4-hydroxy-but-2-enyloxymethyl)-ethyl]-carbamic acid 9H-fluoren-9-ylmethyl ester 
• 183794-27-6 [(S)-2-(4-Benzyloxy-phenyl)-1-((2S,3R)-3-hydroxymethyl-oxiranylmethoxymethyl)-ethyl]-carbamic acid 9H-fluoren-9-ylmethyl ester 

Relevant articles and documents

Formation of the 7-oxa-1,4,10-triazatricyclo[8.2.25,12]tetradecane-2,14-dione ring system: Misrouted synthesis of a peptidomimetic

An attempted synthesis of the tricyclic peptidomimetic 1, designed to imitate a β-turn tripeptide in tendamistat, afforded instead the 6,6,8-ring system of 2. The key step in the synthesis entailed acylation of the hindered α,α'-disubstituted morpholine 4.2, which was approached by acylative ring opening of the 3,6-oxazabicyclo[4.2.0]octane 4.3. However, transannular rather than exocyclic cleavage occurred, giving the 1,6-oxazacyclooctane isomer 4.5. Subsequent ring closures to form the bi- and tricyclic intermediates 7.3 and 8.5 were difficult because of the strain being built into the ring systems. After completion of the synthesis, the structures of the intermediates and final product were elucidated by NMR, with three-bond, heteronuclear multiple-bond correlation experiments providing unambiguous evidence for the ring connectivity, and by molecular modeling, which allowed assignment of the stereochemistry. Compound 2 is a modest inhibitor of the target enzyme α-amylase (K(i) = 170 μM in 5% DMSO/water), binding with similar affinity to the tripeptide Ac-Trp-Arg-Tyr-OMe. Although the side-chain attachment points in the ring system of 2 correspond closely to the relative Cα-positions in tendamistat (rmsd = 0.24 A), the alignment of the Cα-Cβ bonds is poor, illustrating the importance of side-chain orientation in a peptidomimetic.