182216-97-3

Basic information

• Product Name: (3R,4R,5S,1'R)-3-[N-(benzyloxycarbonyl)amino]-5-(1-hydroxyethyl)-4-methoxytetrahydrofuran-2-one
• Synonyms: (3R,4R,5S,1'R)-3-[N-(benzyloxycarbonyl)amino]-5-(1-hydroxyethyl)-4-methoxytetrahydrofuran-2-one
• CAS NO: 182216-97-3
• Molecular Weight: 309.319
• Mol File: 182216-97-3.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: (3R,4R,5S,1'R)-3-[N-(benzyloxycarbonyl)amino]-5-(1-hydroxyethyl)-4-methoxytetrahydrofuran-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: (3R,4R,5S,1'R)-3-[N-(benzyloxycarbonyl)amino]-5-(1-hydroxyethyl)-4-methoxytetrahydrofuran-2-one(182216-97-3)
• EPA Substance Registry System: (3R,4R,5S,1'R)-3-[N-(benzyloxycarbonyl)amino]-5-(1-hydroxyethyl)-4-methoxytetrahydrofuran-2-one(182216-97-3)

Safety Data

• Hazardous Substances Data: 182216-97-3(Hazardous Substances Data)

Upstream product

• 501-53-1 benzyl chloroformate 
• 182216-93-9 (R)-((2R,5S)-3,6-Diethoxy-5-isopropyl-2,5-dihydro-pyrazin-2-yl)-((4R,5R)-2,2,5-trimethyl-[1,3]dioxolan-4-yl)-methanol 
• 182216-94-0 (3R,6S,1'R,2'S,3'R)-2,5-diethoxy-3,6-dihydro-3-(2,3-isopropylidenedioxy-1-methoxybutyl)-6-isopropylpyrazine 
• 182216-95-1 ethyl (2R,3R,4S,5R)-2-amino-4,5-isopropylidenedioxy-3-methoxyhexanoate 
• 182216-96-2 ethyl (2R,3R,4S,5R)-2-[N-(benzyloxycarbonyl)amino]-4,5-isopropylidenedioxy-3-methoxyhexanoate 

Downstream Products

• 182216-98-4 (3R,4R,5S,1'R)-3-[N-(benzyloxycarbonyl)amino]-5-[1-(isopropyldimethylsilanyloxy)ethyl]-4-methoxytetrahydrofuran-2-one 

Relevant articles and documents

Amino acid based diastereoselective synthesis of fucosamines

Enantiomerically pure (+)-D-fucosamine 1, (+)-N-methyl-D-fucosamine 2 and (+)-3-O-methyl-D-fucosamine 3 (elsaminose) have been synthesised from known building blocks derived from natural amino acids. Direct and diastereoselective construction of the key intermediate 8 was accomplished by a highly syn,anti-selective aldol reaction between lithiated Schoellkopf's bis-lactim ether 7 and the 1,3-dioxolane-4-carboxaldehyde 5. Elaboration of the common intermediate required optional methylation, selective hydrolysis of the bis-lactim ether in the presence of an isopropylidene ketal, lactonization and partial reduction of the carboxylic group.