76249-56-4

Basic information

• Product Name: (2S,4R)-2,5-Diamino-4-hydroxypentansaeure-hydrochlorid
• CAS NO: 76249-56-4
• Molecular Weight: 184.623
• Mol File: 76249-56-4.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (2S,4R)-2,5-Diamino-4-hydroxypentansaeure-hydrochlorid(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,4R)-2,5-Diamino-4-hydroxypentansaeure-hydrochlorid(76249-56-4)
• EPA Substance Registry System: (2S,4R)-2,5-Diamino-4-hydroxypentansaeure-hydrochlorid(76249-56-4)

Safety Data

• Hazardous Substances Data: 76249-56-4(Hazardous Substances Data)

Upstream product

• 146952-05-8 (4R)-5-amino-4-hydroxy-2-(hydroxyimino)pentansaeure 

Relevant articles and documents

Ring-Opening Reactions of 1,2-Didehydroprolines, I. - Synthesis of 4-Hydroxyornithine and Protected 4-Amino-3-hydroxybutyronitriles

The cyclic azomethines 6a, b, d and f easily undergo ring-opening reaction with hydroxylamine and its O-alkyl derivatives leading to the oximino compounds 3a, b, d and f-i.Dissolved alkali metals in amines (Birch conditions) give satisfactory yields of reduction products with a stereochemistry depending on the substitution pattern in 3b, d, f-i.In case of 3d, the (2R,4R) stereoisomer 9b is the sole product, which can subsequently be cleaved to give 8b.Compounds 3g-i give predominantly the (2S,4R) product 8a.Acylation under alkaline conditions decarboxylates the oximino compounds 3b and d to the corresponding protected butyronitriles 14a-h.Trifluoroacetic anhydride tranforms 3b into the nitrile 14i together with the cyclization product 15.Key Words: 1,2-Didehydroprolines / Oxime reduction / Ornithine derivatives / Butyronitriles / 2-Piperidones / Proline derivatives / Amino acids