187160-31-2

Upstream product

• 187160-30-1 (3aR,5S,7aS)-5-Azido-2,2-dimethyl-hexahydro-benzo[1,3]dioxole 
• 187160-29-8 Methanesulfonic acid (3aR,5R,7aS)-2,2-dimethyl-hexahydro-benzo[1,3]dioxol-5-yl ester 
• 200340-46-1 Methanesulfonic acid (3aR,5S,7aS)-2,2-dimethyl-hexahydro-benzo[1,3]dioxol-5-yl ester 
• 121573-17-9 (3aR,7aS)-2,2-dimethyltetrahydrobenzo[d][1,3]dioxol-5(6H)-one 

Downstream Products

• 200340-56-3 (1S,3R,4S)-1-azido-4-benzoyloxy-3-hydroxy-cyclohexane 
• 200340-58-5 (1S,3R,4S)-1-azido-3-benzoyloxy-4-hydroxy-cyclohexane 
• 152614-12-5 tert-butyl (1R,2R,4S)-2-hydroxy-7-azabicyclo[2.2.1]heptane-7-carboxylate 
• 163513-98-2 (-)-(1R,4S)-tert-butyl 2-oxo-7-azabicyclo[2.2.1]heptane-7-carboxylate 
• 200340-64-3 (1R,2R,4S)-2-benzoyloxy-7-azabicyclo[2.2.1]heptane 
• 200340-62-1 Benzoic acid (1R,2S,5S)-5-amino-2-methanesulfonyloxy-cyclohexyl ester 
• 200340-60-9 Benzoic acid (1R,2S,5S)-5-azido-2-methanesulfonyloxy-cyclohexyl ester 
• 200340-68-7 Benzoic acid (1S,2R,4S)-4-azido-2-methanesulfonyloxy-cyclohexyl ester 

Relevant academic research and scientific papers

A unified asymmetric approach to substituted hexahydroazepine and 7-azabicyclo[2.2.1]heptane ring systems from D(-)-quinic acid: Application to the formal syntheses of (-)-balanol and (-)-epibatidine

3,4-O-Isopropylidene-3(R),4(S)-dihydroxycyclohexanone 7, a chiron easily prepared through a five step sequence from D(-)-quinic acid 1, has been efficiently utilized as the starting building block for the enantioselective syntheses of (3R,4S)-N-p-toluenesulfonyl-3,4-epoxy-hexahydroazepine 17 and (1R,4S)-N-tert-butoxycabonyl-7-azabicyclo[2.2.1]heptan-2-one 43, advanced intermediates already taken to (-)-balanol and (-)-epibatidine respectively. While the nitrogen atom ring insertion via Beckmann rearrangement was the key step for the construction of the hexahydroazepine ring of 17, a regio- and stereospecific intramolecular nucleophilic ring opening of an intermediate cyclic sulfate featured the approach to the substituted 7-azabicyclo[2.2.1]heptane nucleus of 43.

Enantioselective approach to 7-azabicyclo[2.21lheptane ring systems using D-(-)quinic acid as the chiral educt: Application to the formal synthesis of (+)-epibatidine

By utilizing, D-(-)-quinic acid as the chiral starting material the optically pure 7-[(1,1-dimethylethoxy)carbonyl]-7-azabicyclo[ 2.2.1]heptan-2-one 2, an advanced intermediate already taken to (+)-epibatidine 1, a non-opioid analgesic isolated from Ecuadorian poison frogs, was synthetized through a facile, regioselective intramolecular nucleophilic ring opening of a cyclic sulfate moiety.