164738-22-1

Basic information

• Product Name: (3S,4S)-N-p-toluenesulfonyl-4-azido-3-hydroxy-hexahydroazepine
• Synonyms: (3S,4S)-N-p-toluenesulfonyl-4-azido-3-hydroxy-hexahydroazepine
• CAS NO: 164738-22-1
• Molecular Weight: 310.377
• Mol File: 164738-22-1.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (3S,4S)-N-p-toluenesulfonyl-4-azido-3-hydroxy-hexahydroazepine(CAS DataBase Reference)
• NIST Chemistry Reference: (3S,4S)-N-p-toluenesulfonyl-4-azido-3-hydroxy-hexahydroazepine(164738-22-1)
• EPA Substance Registry System: (3S,4S)-N-p-toluenesulfonyl-4-azido-3-hydroxy-hexahydroazepine(164738-22-1)

Safety Data

• Hazardous Substances Data: 164738-22-1(Hazardous Substances Data)

Upstream product

• 189013-32-9 (3S,4R)-N-p-toluenesulfonyl-3,4-epoxy-hexahydroazepine 
• 200340-37-0 (3R,4S)-N-p-toluenesulfonyl-4-azido-3-benzoyloxy-hexahydroazepine 
• 200340-40-5 Methanesulfonic acid (3R,4S)-4-azido-1-(toluene-4-sulfonyl)-azepan-3-yl ester 
• 200340-11-0 (3aR,8aS)-2-Phenyl-5-(toluene-4-sulfonyl)-hexahydro-[1,3]dioxolo[4,5-c]azepine 
• 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 
• 200340-43-8 (3S,4S)-N-p-toluenesulfonyl-3-acetyloxy-4-azido-hexahydroazepine 
• 918954-25-3 3-[(4-methylphenyl)sulfonyl]perhydrooxireno[2,3-c]azepine 

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.

Total Synhesis of Balanol, Part 1. Enantioselective Synthesis of the Hexahydroazepine Ring via Chiral Epoxides and Azidirines

Three differents routes to the hexahydroazepine unit of the natural products balanol (1) and ophicordin (2) are described.The common starting material is the chiral epoxy alcohol 3 which is converted to the balanol degradation product 10 (Scheme 1) or to