202473-19-6

Basic information

• Product Name: (2S,3S,4S)-N-benzyloxycarbonyl-3-hydroxy-4-azidoproline benzyl ester
• Synonyms: (2S,3S,4S)-N-benzyloxycarbonyl-3-hydroxy-4-azidoproline benzyl ester
• CAS NO: 202473-19-6
• Molecular Weight: 396.403
• Mol File: 202473-19-6.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: (2S,3S,4S)-N-benzyloxycarbonyl-3-hydroxy-4-azidoproline benzyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,3S,4S)-N-benzyloxycarbonyl-3-hydroxy-4-azidoproline benzyl ester(202473-19-6)
• EPA Substance Registry System: (2S,3S,4S)-N-benzyloxycarbonyl-3-hydroxy-4-azidoproline benzyl ester(202473-19-6)

Safety Data

• Hazardous Substances Data: 202473-19-6(Hazardous Substances Data)

Upstream product

• 1414607-48-9 C₁₃H₁₄N₄O₄ 
• 37073-89-5 [(3aR,5S,6S,6aR)-5-((R)-1,2-Dihydroxy-ethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl]-carbamic acid benzyl ester 
• 1414607-46-7 C₁₄H₁₆N₄O₅ 
• 1414607-62-7 benzyl (3aR,4aS,5S,7aS,7bR)-5-azido-2,2-dimethylhexahydro-7H-[1,3]dioxolo[4,5]furo[3,2-b]pyrrole-7-carboxylate 
• 84730-22-3 (1S,3R,7R,8S,11R)-9-<(benzyloxy)carbonyl>-11-<(methylsulfonyl)oxy>-5,5-dimethyl-2,4,6-trioxa-9-azatricyclo<6.3.0.0^3,7>undecane 
• 1414607-58-1 3-[(benzyloxycarbonyl)amino]-3-deoxy-1,2-O-isopropylidene-5,6-di-O-mesyl-α-D-glucofuranose 
• 1414607-55-8 (3S,4S)-4-azido-1-[(benzyloxy)carbonyl]-3-hydroxy-L-proline 
• 100-39-0 benzyl bromide 
• 501-53-1 benzyl chloroformate 
• 13500-53-3 N-benzyloxycarbonyl-(2S,4R)-4-hydroxyproline benzyl ester 
• 159651-34-0 (1S,2S,5R)-6-oxa-3-aza-bicyclo[3.1.0]hexane-2,3-dicarboxylic acid dibenzyl ester 
• 13504-85-3 (2S,4R)-1-(benzyloxycarbonyl)-4-hydroxypyrrolidine-2-carboxylic acid 
• 51-35-4 4R-4-hydroxyproline 
• 159551-87-8 (2S,4R)-N^α-Cbz-4-[(p-toluenesulfonyl)oxy]proline benzyl ester 

Downstream Products

• 202473-18-5 (2S,3R,4S)-3-hydroxy-4-aminoproline 

Relevant articles and documents

Synthesis of protected 4-amino- and 4-azido-3-hydroxy-l-prolines from d-glucose

Differentially protected 4-azido- or 4-amino-3-hydroxy-l-prolines were synthesized in good overall yields (21-31%) from d-glucose. The synthetic strategy involved conversion of d-glucose into 3-[(benzyloxycarbonyl)amino]-3- deoxy-1,2-O-isopropylidene-α-d-glucofuranose, which was subjected to mesylation of the 5- and 6-hydroxy groups and subsequent intramolecular S N2 displacement of the 6-O-mesyl group by the 3-(benzyloxycarbonyl) amino group to give a pyrrolidine ring. The resulting intermediate underwent intermolecular SN2 displacement of the 5-O-mesyl group with sodium azide, hydrolysis of 1,2-acetonide group, treatment with sodium periodate, and Pinnick oxidation to give the required compounds. Georg Thieme Verlag Stuttgart New York.