508205-10-5

Upstream product

• 508204-89-5 (1S,2S,6R,7S,9S)-8-(2-Benzyloxycarbonylamino-acetyl)-4,4-dimethyl-3,5-dioxa-8-aza-tricyclo[5.2.2.0^2,6]undecane-9-carboxylic acid ethyl ester 
• 508204-87-3 (1S,2S,6R,7S,9S)-4,4-Dimethyl-3,5-dioxa-8-aza-tricyclo[5.2.2.0^2,6]undecane-9-carboxylic acid ethyl ester 
• 851389-16-7 ethyl (1S,3S,4S,5S,6R)-5,6-dihydroxy-2-[(1R)-1-phenylethyl]-2-azabicyclo[2.2.2]octane-3-carboxylate 
• 508205-07-0 ethyl (1S,3S,4S,5S,6R)-5,6-dihydroxy-2-azabicyclo[2.2.2]octane-3-carboxylate 
• 134984-64-8 exo-2-aza-2-<(R)-1-phenylethyl>-3-ethoxycarbonyl<2.2.2>bicyclooct-5-ene 
• 508204-96-4 ethyl (1S,3S,4S,5S,6R)-2-(2-benzyloxycarbonylaminoacetyl)-5,6-dihydroxy-2-azabicyclo[2.2.2]octane-3-carboxylate 
• 508204-84-0 (1S,2S,6R,7S,9S)-4,4-Dimethyl-8-((R)-1-phenyl-ethyl)-3,5-dioxa-8-aza-tricyclo[5.2.2.0^2,6]undecane-9-carboxylic acid ethyl ester 

Relevant academic research and scientific papers

An improved cyclization protocol for the synthesis of diazabicyclo[4.3.0] alkanes

We have recently described the synthesis of diazabicyclo[4.X.0]alkanes and their use as ligands for the prostate specific membrane antigene (PSMA). The key step of our synthetic route toward these diazabicycloalkanes is an oxidative cleavage of a bicyclic diol moiety followed by the attack of a nitrogen nucleophile to the resulting intermediate bisaldehyde. We herein describe the mechanism of this ring closure and its stereochemical consequences. In addition, we report a convenient method for trapping intermediate bisaldehydes by Wittig reagents. This trapping allows the synthesis of 3,5-disubstituted proline derivatives, which are shown to be versatile precursors for functionalized diazabicycloalkane dipeptide mimetics.

Efficient synthesis of structurally diverse diazabicycloalkanes: Scaffolds for modular dipeptide mimetics with tunable backbone conformations

A stereoselective synthesis of new dipeptide mimetics based on a diazabicycloalkane scaffold is reported. The route starts from enantiomerically pure azabicycloalkenes 1 that are bis-(hydroxylated) and coupled N-terminally to a second amino acid. The key step of the reaction sequence is an oxidative cleavage of the resulting dipeptides 5 to give highly functionalised diazabicycloalkanes 6, which can be easily converted into a number of dipeptide mimetics with defined and variable stereochemistry and a number of different amino acid side chains. The backbone dihedral angles within these dipeptide mimetics can be tuned by varying the stereochemistry and the ring sizes of the diazabicycloalkane scaffold. The syntheses of conformationally constrained dipeptide analogues in four to five steps are presented. With the syntheses of dipeptide mimetics 19a-c, suitable linker moieties for conjugation of diazabicycloalkanes to other functional molecules like markers or solid phases are introduced, making these compounds modular dipeptide mimetics that might find applications as modular ligands or as solid-phase-attached scaffolds in combinatorial chemistry. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.

Short and efficient synthesis of diazabicycloalkane dipeptide mimics

A new synthetic route to enantiomerically pure diazabicycloalkanes is reported. Key step of this synthesis is an oxidative cleavage of azabicycloalkene precursors that are synthesized in enantiomerically pure form via aza-Diels-Alder reaction. A range of diazabicycloalkanes with different amino acid side chains have been synthesized and their structure has been elucidated by NMR analysis.