54230-53-4

Upstream product

• 116233-65-9 4-exo-acetoxy-3-endo-methoxy-6-aza-2-oxabicyclo<3.2.1>octan-7-one 
• 116233-64-8 4-exo-acetoxy-3-endo-methoxy-6-<(R)-1-(p-methoxyphenyl)ethyl>-6-aza-2-oxabicyclo<3.2.1>octan-7-one (D) 
• 116233-63-7 4-exo-hydroxy-3-endo-methoxy-6-<((R)-1-methoxyphenyl)ethyl>-6-aza-2-oxabicyclo<3.2.1>octan-7-one (D) 
• 116233-62-6 6-<(R)-1-(p-methoxyphenyl)ethyl>-6-aza-2-oxabicyclo-<3.2.1>oct-3-en-7-one 
• 116233-66-0 1-O-methyl-β,D-ezoaminouric acid 
• 116233-57-9 4-exo-bromo-6-<(R)-1-(p-methoxyphenyl)ethyl>-6-aza-2-oxabicyclo<3.2.1>octan-7-one 
• 116233-55-7 N-<(R)-1-(p-methoxyphenyl)ethyl>-2,5-dihydro-6H-pyran-6-carboxamide 
• 24588-58-7 diethyl 3,6-dihydro-2H-pyran-2,2-dicarboxylate 
• 116233-54-6 3,6-dihydro-2H-pyran-2-carboxylic acid 
• 98-88-4 benzoyl chloride 
• 54230-54-5 (2S,4S,5R,6R)-4-Amino-5-hydroxy-6-methoxy-tetrahydro-pyran-2-carboxylic acid methyl ester 

Relevant academic research and scientific papers

Synthesis of 1-O-Methyl-β,D-ezoaminouoic Acid

The synthesis of the title compound from the Diels-Alder adduct of diethyl ketomalonate and 1,3-butadiene (nine steps, 13percent overall yield) is described.The key step is a transannular "bromolactamization" reaction, which sets up the stereocontrolled functionalization of the pyran ring.The use of resolved p-methoxyenethylamine as the source of the amino group allows the synthesis of both the D (natural) and L (unnatural) series amino sugars.