247096-94-2

Upstream product

• 99-76-3 methyl 4-hydroxylbenzoate 
• 247096-93-1 9-O-tert-butyldimethylsilyl-10,11-dihydro-11-iodo-quinidine 
• 205432-44-6 (3R,4S,8R,9S)-9-{[tert-butyl(dimethyl)silyl]oxy}-6'-methoxycinchonan 
• 247096-92-0 9-O-tert-butyldimethylsilyl-10,11-dihydro-11-tosyloxy-quinidine 
• 247096-89-5 9-O-tert-butyldimethylsilyl-10,11-dihydro-11-hydroxyquinidine 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 56-54-2 quinindine 

Downstream Products

• 219596-40-4 methyl 10,11-dihydroquinidine-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.