452084-60-5

Basic information

• Product Name: tert-butyl (3S,4R)-4-(benzyloxy)-3-((tert-butyldimethylsilyl)oxy)azepane-1-carboxylate
• Synonyms: tert-butyl (3S,4R)-4-(benzyloxy)-3-((tert-butyldimethylsilyl)oxy)azepane-1-carboxylate
• CAS NO: 452084-60-5
• Molecular Weight: 435.679
• Mol File: 452084-60-5.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: tert-butyl (3S,4R)-4-(benzyloxy)-3-((tert-butyldimethylsilyl)oxy)azepane-1-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: tert-butyl (3S,4R)-4-(benzyloxy)-3-((tert-butyldimethylsilyl)oxy)azepane-1-carboxylate(452084-60-5)
• EPA Substance Registry System: tert-butyl (3S,4R)-4-(benzyloxy)-3-((tert-butyldimethylsilyl)oxy)azepane-1-carboxylate(452084-60-5)

Safety Data

• Hazardous Substances Data: 452084-60-5(Hazardous Substances Data)

Upstream product

• 69739-34-0 t-butyldimethylsiyl triflate 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 263889-21-0 (3S,4R)-4-benzyloxy-3-hydroxy-2,3,4,7-tetrahydroazepine-1-carboxylic acid tert-butyl ester 
• 452084-58-1 [(1S,2R)-1-Azidomethyl-2-benzyloxy-5-(4-methoxy-benzyloxy)-pentyloxy]-tert-butyl-dimethyl-silane 
• 452084-65-0 (2S,3R)-3-Benzyloxy-6-(4-methoxy-benzyloxy)-hexane-1,2-diol 
• 452084-63-8 (2S,3R)-1-Azido-3-benzyloxy-6-(4-methoxy-benzyloxy)-hexan-2-ol 
• 452084-64-9 (S)-4-[(R)-1-Benzyloxy-4-(4-methoxy-benzyloxy)-butyl]-2,2-dimethyl-[1,3]dioxolane 
• 452084-67-2 (4R,5S)-6-Azido-4-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-hexan-1-ol 
• 452084-56-9 (S)-2-[(R)-1-Benzyloxy-4-(4-methoxy-benzyloxy)-butyl]-oxirane 
• 452084-52-5 (R)-4-Benzyloxy-4-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-butan-1-ol 
• 452084-62-7 (R)-4-(4-Methoxy-benzyloxy)-1-(S)-oxiranyl-butan-1-ol 
• 452084-51-4 (S)-4-((R)-1-Benzyloxy-but-3-enyl)-2,2-dimethyl-[1,3]dioxolane 
• 142561-89-5 (R)-1-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)but-3-en-1-ol 
• 154476-70-7 6-(4-methoxybenzyloxy)hex-1-en-3-ol 

Downstream Products

• 158980-65-5 1,1-dimethylethyl (3R)-trans-hexahydro-4-hydroxy-3-{[4-(phenylmethoxy)benzoyl]amino}-1H-azepine-1-carboxylate 
• 452084-61-6 tert-butyl (3R,4R)-3-azido-4-(benzyloxy)azepane-1-carboxylate 
• 452084-66-1 tert-butyl (3S,4R)-4-(benzyloxy)-3-hydroxyazepane-1-carboxylate 

Relevant articles and documents

Synthesis of Substituted Oxo-Azepines by regioand diastereoselective Hydroxylation

Substituted seven-membered N-heterocycles are prevalent bioactive epitopes and useful synthons for preparing enzyme inhibitors or molecular recognition systems. To fully exploit the chemical properties of this flexible N-heterocycle scaffold, efficient methods for its diverse functionalization are required. Here we utilize the late-stage oxidation of tetrahydroazepines as an approach to access densely functionalized oxo-azepines in a total of 8 steps and ~30% overall yield from commercially available starting materials. Hydroboration of tetrahydroazepines proceeded with diastereoselectivity in a substrate-dependent manner to yield regioisomeric azepanols before their oxidation to the corresponding oxo-azepines. Regioselectivity of the hydroboration step may be improved moderately by a rhodium catalyst, albeit with loss of conversion to a competing hydrogenation pathway. Overall our method allows efficient access to azepanols and oxo-azepines as versatile epitopes and synthons with a high degree of diastereoselectivity and moderate regioselectivity.