477191-16-5

Basic information

• Product Name: (R)-β-hydroxy-N-(benzenesulfonyl)valine
• Synonyms: (R)-β-hydroxy-N-(benzenesulfonyl)valine
• CAS NO: 477191-16-5
• Molecular Weight: 273.31
• Mol File: 477191-16-5.mol

Chemical Properties

• CAS DataBase Reference: (R)-β-hydroxy-N-(benzenesulfonyl)valine(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-β-hydroxy-N-(benzenesulfonyl)valine(477191-16-5)
• EPA Substance Registry System: (R)-β-hydroxy-N-(benzenesulfonyl)valine(477191-16-5)

Safety Data

• Hazardous Substances Data: 477191-16-5(Hazardous Substances Data)

Upstream product

• 477191-15-4 (2S)-2-N-(benzenesulfonyl)amino-3-methyl-1,3-butanediol 

Relevant articles and documents

Serine as chiral educt for the practical synthesis of enantiopure N-protected β-hydroxyvaline

N-tert-Butyloxycarbonyl- and N-benzenesulfonyl-β-hydroxyvalines 1a and 1b were, respectively, synthesized in enantiomerically pure form by a two-step protocol from their enantiomeric N-protected serine methyl esters 2a and 2b. The addition of CH3MgBr to 2a and 2b provided diols 3a and 3b, respectively as major products in 83% and 81% yields. Selective oxidation of diols 3a and 3b was performed using a TEMPO, NaClO2, NaOCl cocktail in 96% and 93% respective yields. This two-step process effectively furnished multigram amounts of enantiopure N-Boc-β-hydroxyvaline 1a.