200340-27-8

Basic information

• Product Name: (3R,4R)-N-p-toluenesulfonyl-4-benzoyloxy-3-hydroxy-hexahydroazepine
• Synonyms: (3R,4R)-N-p-toluenesulfonyl-4-benzoyloxy-3-hydroxy-hexahydroazepine
• CAS NO: 200340-27-8
• Molecular Weight: 389.472
• Mol File: 200340-27-8.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (3R,4R)-N-p-toluenesulfonyl-4-benzoyloxy-3-hydroxy-hexahydroazepine(CAS DataBase Reference)
• NIST Chemistry Reference: (3R,4R)-N-p-toluenesulfonyl-4-benzoyloxy-3-hydroxy-hexahydroazepine(200340-27-8)
• EPA Substance Registry System: (3R,4R)-N-p-toluenesulfonyl-4-benzoyloxy-3-hydroxy-hexahydroazepine(200340-27-8)

Safety Data

• Hazardous Substances Data: 200340-27-8(Hazardous Substances Data)

Upstream product

• 200340-24-5 (3aR,8aS)-5-(Toluene-4-sulfonyl)-hexahydro-1,3-dioxa-2-thia-5-aza-azulene 2,2-dioxide 
• 200339-98-6 (3aR,8aS)-2,2-Dimethyl-5-(toluene-4-sulfonyl)-hexahydro-[1,3]dioxolo[4,5-c]azepine 
• 200340-07-4 (3R,4S)-N-p-toluenesulfonyl-3,4-dihydroxy-hexahydroazepine 
• 200339-89-5 (5S,6R)-5,6-O-isopropylidene-azepane-2-one 
• 1863-63-4 ammonium benzoate 

Downstream Products

• 200340-31-4 Benzoic acid (3R,4R)-3-methanesulfonyloxy-1-(toluene-4-sulfonyl)-azepan-4-yl ester 
• 189013-32-9 (3S,4R)-N-p-toluenesulfonyl-3,4-epoxy-hexahydroazepine 

Relevant articles and documents

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.