58107-45-2

Basic information

• Product Name: methyl (2S,3R)-N-(p-toluenesulfonyl)-3-amino-3-phenyl-2-hydroxypropanoate
• Synonyms: methyl (2S,3R)-N-(p-toluenesulfonyl)-3-amino-3-phenyl-2-hydroxypropanoate
• CAS NO: 58107-45-2
• Molecular Weight: 349.408
• Mol File: 58107-45-2.mol

Chemical Properties

• CAS DataBase Reference: methyl (2S,3R)-N-(p-toluenesulfonyl)-3-amino-3-phenyl-2-hydroxypropanoate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl (2S,3R)-N-(p-toluenesulfonyl)-3-amino-3-phenyl-2-hydroxypropanoate(58107-45-2)
• EPA Substance Registry System: methyl (2S,3R)-N-(p-toluenesulfonyl)-3-amino-3-phenyl-2-hydroxypropanoate(58107-45-2)

Safety Data

• Hazardous Substances Data: 58107-45-2(Hazardous Substances Data)

Upstream product

• 127-65-1 chloroamine-T 
• 103-26-4 Methyl cinnamate 
• 825627-55-2 methyl (3R)-2-diazo-3-phenyl-3-[(N-tosyl)amino]propanoate 
• 825627-66-5 methyl (3R)-2-oxo-3-phenyl-3-[(N-tosyl)amino]propanoate 
• 144-86-5 N-chloro-4-methylbenzenesulfonamide 

Relevant articles and documents

A highly stereoselective addition of the anion derived from α-diazoacetamide to aromatic N-tosylimines

In the presence of an Evans oxazolidinone as the chiral auxiliary, the anion derived from α-diazoacetamide adds to aromatic N-tosylimines with high stereoselectivity (see scheme). The addition products can be used in a concise and stereoselective synthesi

Heterogeneous catalytic asymmetric aminohydroxylation of olefins using polymer-supported cinchona alkaloids

For the first time, heterogeneous osmium tetroxide catalyzed asymmetric aminohydroxylation of olefins on polymer-supported ligands have been shown to proceed with comparable rate as in the case of homogeneous conditions.

Catalytic asymmetric aminohydroxylation provides a short taxol side-chain synthesis.

The p-toluenesulfonamide derivate of the C-13 side-chain of taxol was prepared on a one third mole scale in a single step from methyl cinnamate. The process employed is catalytic asymmetric aminohydroxylation (catalytic AA). In the present case, there is no work-up other than filtration of the pure product which is insoluble in the reaction mixture. The sulfonamide protecting group is removed by acidic hydrolysis.

Katalytische asymmetrische Aminohydroxylierung (AA) von Olefinen

Keywords: β-Aminoalkohole; Asymmetrische Aminohydroxylierung; Chloramin T; Osmiumverbindungen; Taxolseitenkette