73473-40-2

Usage

Chemical Properties

Off-white solid

Upstream product

• 73473-34-4 2-<(2S)-2-Methoxymethyl-1-pyrrolidinylmethyleneamino>-2-methylbutanoic acid, methyl ester 
• 118995-18-9 (2S,4R)-3-benzoyl-4-ethyl-4-methyl-2-phenyl-1,3-oxazolidin-5-one 
• 123254-58-0 (R)-2-((tert-butoxycarbonyl)amino)-2-methylbutanoic acid 
• 3059-97-0 (2R)-2-amino-2-methylbutanoic acid 

Downstream Products

• 78410-93-2 (R)-methyl 2-(amino)-2-methylbutanoate 
• 123254-58-0 (R)-2-((tert-butoxycarbonyl)amino)-2-methylbutanoic acid 

Relevant academic research and scientific papers

A practical chemoenzymatic synthesis of (R)-isovaline based on the asymmetric hydrolysis of 2-ethyl-2-methyl-malonamide

(R)-Isovaline has potential applications in drug development, and therefore the development of an efficient method for the production of (R)-isovaline is desired. Herein we have investigated the asymmetric hydrolysis of 2-ethyl-2-methyl-malonamide into (S)-2-ethyl-2-methyl-malonamic acid, a useful synthetic intermediate in the production of (R)-isovaline, using CsAM, which is a recombinant amidase originally derived from Cupriavidus sp. KNK-J915. The produced (S)-2-ethyl-2-methyl-malonamic acid (98.6% ee) could be easily converted into (R)-isovaline by the Hofmann rearrangement. Starting from diethyl 2-methylmalonate, we obtained (R)-isovaline (99.1% ee) in 58.6% yield over eight steps, including the CsAM-catalyzed asymmetric hydrolysis of 2-ethyl-2-methyl-malonamide.

Preparation and synthetic applications of (S)- and (R)-N-boc-N, O- isopropylidene-α-methylserinals: Asymmetric synthesis of (S)- and (R)-2- amino-2-methylbutanoic acids (Iva)

This report describes an efficient and convenient large-scale synthesis procedure for (S)- and (R)-N-Boc-α-methylserinal acetonides (3 and 4) starting from (R)-2-methylglycidol 5. The application of both of these compounds as valuable chiral building blocks in the asymmetric synthesis of α-methylamino acids is also demonstrated by the synthesis of (S)- and (R)- isovalines (Iva) (6 and 7).

Asymmetric Synthesis of α-Substituted Amino Acids and Amines by Carbon-Carbon Bond Formation in Position α to the Nitrogen

The asymmetric synthesis of α-substituted α-amino acids and propargylamines is described.As chiral auxiliary we used (S)-(-)-1-dimethoxymethyl-2-methoxymethylpyrrolidine (SDMP, 1).Treatment of the amino acids or amines with SDMP 1 afforded the correspondi