356048-03-8

Upstream product

• 147501-89-1 (R)-2,3-dihydroxy-2-methyl-propionic acid methyl ester 
• 356048-01-6 methyl (4R)-4-methyl-2-oxo-2λ⁴-[1,3,2]dioxathiolane-4-carboxylate 
• 356048-06-1 methyl (4R)-4-methyl-2-dioxo-2λ⁶-[1,3,2]dioxathiolane-4-carboxylate 

Downstream Products

• 866555-08-0 (S)-2-Azido-3-hydroxy-2-methyl-propionic acid 
• 188476-33-7 (S)-2-N-(tert-butoxycarbonyl)amino-2-methyl-3-hydroxypropanoic acid methyl ester 

Relevant academic research and scientific papers

Synthesis of a new conformationally constrained glycoamino acid building block

The synthesis of a suitably protected β-D-glucopyranosyl-(S)-α-methylserine derivative - a new conformationally constrained glycosylated quaternary amino acid analogue of β-D-glucopyranosyl-L-serine - is described. This compound can be used as an attractive building block for the synthesis of new, constrained glycopeptides.

Enantioselective synthesis of (S)- and (R)-α-methylserines: Application to the synthesis of (S)- and (R)-N-Boc-N,O-isopropylidene-α-methylserinals

This report describes the synthesis of enantiomerically pure (S)- and (R)-α-methylserines on a multigram scale, starting from the Weinreb amide of 2-methyl-2-propenoic acid and using a stereodivergent synthetic route that involves a Sharpless asymmetric dihydroxylation reaction. As a synthetic application of these quaternary α-amino acids, they were used as starting materials in the synthesis of the well-known valuable homochiral (S)- and (R)-N-Boc-N,O-isopropylidene-α-methylserinal building blocks.