508205-07-0

Usage

Also known as

(1S,3S,4S,5S,6R)-3,4,5,6-tetrahydroxyazabicyclo[2.2.2]octane ethyl ester

Molecular structure

Complex

Derivative of

2-azabicyclo[2.2.2]octane

Functional groups

Hydroxy, carboxylic acid, ethyl ester

Stereochemistry

(1S,3S,4S,5S,6R)

Potential applications

Pharmaceuticals, agrochemicals, materials science

Upstream product

• 851389-16-7 ethyl (1S,3S,4S,5S,6R)-5,6-dihydroxy-2-[(1R)-1-phenylethyl]-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 

Downstream Products

• 508204-99-7 ethyl (1S,3S,4S,5S,6R)-2-[(2S)-2-benzyloxycarbonylamino-3-methylbutyryl]-5,6-dihydroxy-2-azabicyclo[2.2.2]octane-3-carboxylate 
• 508204-96-4 ethyl (1S,3S,4S,5S,6R)-2-(2-benzyloxycarbonylaminoacetyl)-5,6-dihydroxy-2-azabicyclo[2.2.2]octane-3-carboxylate 
• 697289-80-8 ethyl (1S,3S,4S,5S,6R)-2-[(2S)-2-benzyloxycarbonylamino-3-methoxycarbonylpropionyl]-5,6-dihydroxy-2-azabicyclo[2.2.2]octane-3-carboxylate 
• 697290-10-1 (1R,3S,6S,7S,9aS)-1-Hydroxy-3-methoxycarbonylmethyl-4-oxo-octahydro-pyrido[1,2-a]pyrazine-2,6,7-tricarboxylic acid 2-benzyl ester 6-ethyl ester 
• 697290-08-7 (1R,3S,6S,7S,9aS)-7-Formyl-1-hydroxy-3-methoxycarbonylmethyl-4-oxo-octahydro-pyrido[1,2-a]pyrazine-2,6-dicarboxylic acid 2-benzyl ester 6-ethyl ester 
• 508205-10-5 (6S,7S,9aS)-7-Formyl-1-hydroxy-4-oxo-octahydro-pyrido[1,2-a]pyrazine-2,6-dicarboxylic acid 2-benzyl ester 6-ethyl ester 

Relevant academic research and scientific papers

2-CYANOPYRROLIDINECARBOXAMIDE COMPOUND

A compound of the formula (I) or a pharmaceutically acceptable salt thereof: [wherein X1 and X2 each is independently lower alkylene; X3 is =CH2, =CHF or =CF2; R1 is substituent, R2 and R3 each is independently H or lower alkyl; n is 0, 1, 2, 3 or 4.] having the activity inhibiting DPP-IV activity. They are therefore useful in the treatment of conditions mediated by DPP-IV, such as NIDDM.

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.