138858-47-6

Basic information

• Product Name: tert-butyl (2S,4S)-N-(tert-butoxycarbonyl)-4-benzylpyroglutamate
• Synonyms: tert-butyl (2S,4S)-N-(tert-butoxycarbonyl)-4-benzylpyroglutamate
• CAS NO: 138858-47-6
• Molecular Weight: 375.465
• Mol File: 138858-47-6.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: tert-butyl (2S,4S)-N-(tert-butoxycarbonyl)-4-benzylpyroglutamate(CAS DataBase Reference)
• NIST Chemistry Reference: tert-butyl (2S,4S)-N-(tert-butoxycarbonyl)-4-benzylpyroglutamate(138858-47-6)
• EPA Substance Registry System: tert-butyl (2S,4S)-N-(tert-butoxycarbonyl)-4-benzylpyroglutamate(138858-47-6)

Safety Data

• Hazardous Substances Data: 138858-47-6(Hazardous Substances Data)

Upstream product

• 591-51-5 phenyllithium 
• 144331-21-5 di-tert-butyl (S)-4-methylene-5-oxopyrrolidine-1,2-dicarboxylate 
• 127949-78-4 tert-butyl (2S)-1-(benzyloxycarbonyl)-4β-(hydroxyphenylmethyl)pyroglutamate 
• 138858-39-6 tert-butyl (2S)-4β-(hydroxyphenylmethyl)pyroglutamate 
• 100-52-7 benzaldehyde 
• 81470-51-1 tert-butyl N-benzyloxycarbonyl-L-pyroglutamate 
• 32159-21-0 Cbz-L-pGlu-OH 
• 151121-34-5 di-tert-butyl (2S,4E)-4-[(dimethylamino)methylidene]-5-oxopyrrolidine-1,2-dicarboxylate 
• 124957-36-4 Methyl 3-acetoxy-2-methylene-3-phenylpropanoate 
• 81477-94-3 N-(diphenylmethylene)glycine tert-butyl ester 
• 24424-99-5 di-tert-butyl dicarbonate 
• 868398-01-0 1-(1,1-dimethylethyl) 5-methyl (S)-N-(diphenylmethylene)-(4E)-(phenylmethylene)-L-glutamate 
• 868398-13-4 (S)-5-Oxo-4-[1-phenyl-meth-(E)-ylidene]-pyrrolidine-2-carboxylic acid tert-butyl ester 
• 91229-91-3 tert-butyl (S)-N-tert-butoxycarbonylpyroglutamate 

Relevant articles and documents

Reinvestigation of the alkylation of pyroglutamate ester urethanes

Previous studies by several groups on the alkylation of pyroglutamic acid derivatives have led to a consensus that the stereoselectivity of alkylation at C-4 is invariably trans to the ester group at C-2. We have now discovered that this generalisation is not invariably correct and that, although for S(N)1-type electrophiles stereoselectivity is in fact trans, S(N)2-type electrophiles can give the thermodynamically less stable cis products with high diastereoselectivity. Use of the bulky proton source 2,6- di-tert-butylphenol to quench these reactions yields cis isomers as the only products in good yield, thus making direct alkylation of pyroglutamic acid derivatives a useful starting point for the synthesis of homochiral target compounds.

Catalytic enantioselective synthesis of glutamic acid derivatives via tandem conjugate addition - Elimination of activated allylic acetates under chiral PTC conditions

A new, general, and practical procedure for the asymmetric synthesis of 4-alkylidenyl glutamic acid derivatives via a catalytic enantioselective tandem conjugate addition-elimination on allylic acetates under chiral phase-transfer conditions is reported.

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