194983-28-3

Upstream product

• 194983-30-7 9-O-tert-butyldimethylsilyl-10,11-dihydro-11-iodo-quinine 
• 194983-29-4 9-O-tert-butyldimethylsilyl-10,11-dihydro-11-tosyl-quinine 
• 183994-18-5 2-{(3R,4S,6S)-6-[(R)-(tert-Butyl-dimethyl-silanyloxy)-(6-methoxy-quinolin-4-yl)-methyl]-1-aza-bicyclo[2.2.2]oct-3-yl}-ethanol 
• 99-76-3 methyl 4-hydroxylbenzoate 
• 194983-31-8 methyl 9-O-tert-butyldimethylsilyl-10,11-dihydroquinine-11-(phenoxy-p-carboxylate) 

Relevant academic research and scientific papers

Effects of shape on thermodynamic cyclizations of cinchona alkaloids

Thermodynamic cyclizations of a series of cinchona alkaloid derivatives are investigated. An extended quinine monomer 2:HO-Ce-OMe is prepared and cyclized to produce a mixture of cyclic oligomers. Combining the extended monomer 2:HO-Ce-OMe with the previously reported cinchonidine monomer 1b:HO- Cc-OMe under thermodynamic control produces a library of quinine-derived macrocycles. Two quinidine-derived methyl ester monomers 10:HO-Cd-OMe and 16:HO-Ca-OMe are also reported. Both are preorganized to form cyclic dimers; upon carrying out the thermodynamic cyclization on a mixture of both monomers only a small percentage (5%) of the hetero-dimer is obtained. Thermodynamic cyclization of the corresponding cinchonidine derived methyl ester 1b:HO-Cc- OMe with 10:HO-Cd-OMe results in the self-sorting of the two diastereoisomers.

Building thermodynamic combinatorial libraries of quinine macrocycles

Thermodynamically-controlled transesterification of a predisposed cinchonidine building block with a more flexible extended quinine monomer leads to a combinatorial mixture of 11 macrocyclic receptors which is analysed by electrospray mass spectrometry; s