166756-77-0

Usage

Chemical Properties

white to off-white crystalline powder

InChI:InChI=1/C6H11NO4/c1-3(5(8)9)2-4(7)6(10)11/h3-4H,2,7H2,1H3,(H,8,9)(H,10,11)/p-1/t3-,4-/m1/s1

Upstream product

• 144331-22-6 1-tert-butyl (2S,4S)-N-(tert-butoxycarbonyl)-4-methylglutamic acid 
• 166756-72-5 N-(4-nitrobenzoyl)-D-glutamic acid dimethyl ester 
• 166756-73-6 (2R,4R) N-p-nitrobenzoyl 4-methyl glutamic acid dimethyl ester 
• 7148-24-5 diethyl (4-nitrobenzoyl)-L-glutamate 
• 166756-74-7 (2S,4S)-2-Methyl-4-(4-nitro-benzoylamino)-pentanedioic acid diethyl ester 
• 144345-38-0 (2S,4S)-di-tert-butyl 4-methyl-5-oxopyrrolidine-1,2-dicarboxylate 

Relevant academic research and scientific papers

A Highly Diastereoselective Synthesis of 4-Alkyl Threo Glutamic Acids

Treatment of N-p-nitrobenzoyl L- or D-glutamic acid diester with lithium bis(trimethylsilyl)amide generates a chelated γ-enolate which reacts with alkyl halides to give (2S,4S)- or (2R,4R)-4-alkylated glutamic acid derivatives with very high diastereoselectivity.

Stereospecific synthesis of naturally-occurring 4-alkylideneglutamic acids, 4-alkylglutamates and 4-alkylprolines

The enaminone 4, prepared from (2S)-pyroglutamic acid, has been found to react in an apparent 1,4-manner with DIBAL and Grignard reagents to afford a variety of alkylidene derivatives 8 which, except for the vinyl derivatives 8e, are formed only as the (E

Stereospecific Synthesis of 4-Alkylglutamates and 4-Alkylprolines

Catalytic reduction of the 4-alkylidenepyroglutamate derivatives (3) affords an effective route to (2S,4S)-4-alkylglutamic acids and (2S,4S)-4-alkylprolines.The route has also been used to prepare a 4-alkylpyroglutamic acid derivative which is stereospeci