171898-25-2

Upstream product

• 100-39-0 benzyl bromide 
• 141293-28-9 N-(tert-butoxycarbonyl)-2-[(tert-butyldimethylsilyl)oxy]pyrrole 
• 69739-34-0 t-butyldimethylsiyl triflate 
• 171898-22-9 (+/-)-5-benzyl-1-(tert-butoxycarbonyl)-2,5-dihydropyrrol-2-one 

Downstream Products

• 171898-27-4 (+/-)-5-benzyl-1-(tert-butoxycarbonyl)-5-methyl-2,5-dihydropyrrol-2-one 
• 171898-30-9 (+/-)-N-(tert-butoxycarbonyl)-3-O-(tert-butyldimethylsilyl)-2-benzylserine 
• 146648-27-3 N-(tert-butoxycarbonyl)-α-benzylphenylalanine 
• 1059698-59-7 2-Benzyl-3,4-dihydroxy-2-methyl-5-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 86778-91-8 (+/-)-N-(tert-butoxycarbonyl)-α-methylphenylalanine 
• 6278-96-2 2-amino-2-benzyl-3-phenylpropanoic acid 
• 1132-26-9 2-methyl-3-phenylalanine 
• 171898-29-6 (+/-)-5-benzyl-N-(tert-butoxycarbonyl)-5-(tert-butyldimethylsiloxymethyl)-2,5-dihydropyrrol-2-one 
• 171898-28-5 5,5-dibenzyl-1-(tert-butoxycarbonyl)pyrrolin-2-one 

Relevant academic research and scientific papers

γ-Substituted pyrrole-based silyl dienol ethers as α-amino acid enolate equivalents: a versatile entry to racemic α-substituted α-amino acids

γ-Substituted siloxypyrrole derivatives 5-7 have been synthesized by direct alkylation of N-(tert-butoxycarbonyl)-2-(tert-butyldimethylsiloxy)pyrrole 1.These underwent subsequent alkylation with alkyl halides or aldehydes to produce γ,γ-disubstituted α,β-unsaturated lactam intermediates in good yields.Oxidative cleavage of the C(3)-C(4) bond within the lactam moiety gave rise to a number of α-substituted α-amino acids.These include racemic α-methylphenylalanine 14, α-benzylphenylalanine 15, α-benzylserine 18 and α-methylthreonine 21.

Furan-, pyrrole-, and thiophene-based siloxydienes for syntheses of densely functionalized homochiral compounds

This review describes the methods of preparation and use of 2-(trimethylsiloxy)furan, N-(tert-butoxycarbonyl)-2-(tert-butyldimethylsiloxy)pyrrole, and certain substituted analogues and congeners, including novel 2-(tert-butyldimethylsiloxy)thiophene, to synthesize complex carbohydrates, azasugars, polyhydroxylated alkaloids, C-glycosylated α-amino acids, amino acids bearing quaternary chiral carbon atoms, and thiosugars. Especially emphasized is the preparation of enantiomerically pure compounds of biological interest. Some mechanistic insights are presented.