151963-67-6

Basic information

• Product Name: (2S,9S)-7-Benzyl-2-(carbobenzoxyamino)-10-chloro-9-hydroxy-7-azadecanoic acid benzyl ester
• Synonyms: (2S,9S)-7-Benzyl-2-(carbobenzoxyamino)-10-chloro-9-hydroxy-7-azadecanoic acid benzyl ester
• CAS NO: 151963-67-6
• Molecular Weight: 553.098
• Mol File: 151963-67-6.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (2S,9S)-7-Benzyl-2-(carbobenzoxyamino)-10-chloro-9-hydroxy-7-azadecanoic acid benzyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,9S)-7-Benzyl-2-(carbobenzoxyamino)-10-chloro-9-hydroxy-7-azadecanoic acid benzyl ester(151963-67-6)
• EPA Substance Registry System: (2S,9S)-7-Benzyl-2-(carbobenzoxyamino)-10-chloro-9-hydroxy-7-azadecanoic acid benzyl ester(151963-67-6)

Safety Data

• Hazardous Substances Data: 151963-67-6(Hazardous Substances Data)

Upstream product

• 67843-74-7 (S)-epichlorohydrin 
• 78767-79-0 N^ε-benzyl-N^α-carbobenzoxy-L-lysine benzyl ester 
• 5361-91-1 N_α-benzyloxycarbonyl-L-lysine benzyl ester p-toluenesulfonate 
• 100-52-7 benzaldehyde 

Downstream Products

• 34994-11-1 hypusine 
• 151963-69-8 (2S,9R)-7-Benzyl-2-(carbobenzoxyamino)-10-cyano-9-hydroxy-7-azadecanoic acid benzyl ester 

Relevant articles and documents

Total Syntheses of (+)-Hypusine and Its (2S,9S)-Diastereomer

The total synthesis of (2S,9R)-hypusine dihydrochloride, an unusual amino acid constituent of the eukaryotic translation initiation factor eIF-4D, and its (2S,9S) diastereomer is described.The key step in the syntheses involves Nε-alkylation of Nε-benzyl-Nα-(L)-lysine benzyl ester with (R)- or (S)-epichlorhydrin to give the respective (2S,9R) and (2S,9S) chlorohydrins.Subsequent displacement of the respective chlorides by cyanide ion provides the protected hypusine skeletons.The final step, hydrogenation over PtO2 in AcOH followed by neutralization and reacidification, yielded the respective (2S,9S)- and (2S,9R)-hypusine dihydrochlorides in excess of 50percent overall yield.