82267-26-3

Upstream product

• 501-53-1 benzyl chloroformate 
• 82267-24-1 (R)-4-amino-1,2-butanediol 
• 82267-28-5 [2-((R)-2-Oxo-[1,3]dioxolan-4-yl)-ethyl]-carbamic acid benzyl ester 
• 13139-17-8 N-(Benzyloxycarbonyloxy)succinimide 

Downstream Products

• 82267-37-6 (S)-2-Benzyloxycarbonylamino-6-((R)-4-benzyloxycarbonylamino-2-hydroxy-butylamino)-hexanoic acid benzyl ester 
• 82267-32-1 (R)-4-benzyloxycarbonylamino-1-bromo-2-butanol 
• 260783-38-8 tert-butyl(2S,9R)-11-[(benzyloxycarbonyl)amino]-2-[(tert-butoxycarbonyl)amino]-9-hydroxy-7-azaundecanoate 
• 260783-31-1 (R)-N¹-(tert-butoxycarbonyl)-N⁸-(benzyloxycarbonyl)-6-hydroxyspermidine 
• 260783-30-0 (R)-N-(benzyloxycarbonyl)-3,4-epoxybutylamine 
• 189280-15-7 tert-butyl(2S,9R)-11-[(benzyloxycarbonyl)amino]-2-[(tert-butoxycarbonyl)amino]-9-hydroxy-7-(benzyloxycarbonyl)-7-azaundecanoate 
• 82267-30-9 (R)-4-benzyloxycarbonylamino-1-p-tolylsulfonyloxy-2-butanol 

Relevant academic research and scientific papers

Synthesis of Cyclic and Acyclic β-Amino Acids via Chelation-Controlled 1,3-Dipolar Cycloaddition

Isoxazolidines have been synthesized in diastereomeric excess up to 94% via a MgBr2-induced chelation-controlled 1,3-dipolar cycloaddition reaction with N-hydroxyphenylglycinol as a chiral auxiliary. The diastereomerically pure isoxazolidines were further transformed into cyclic and acyclic β-amino acid derivatives.

(R)- and (S)-N-(Benzyloxycarbonyl)-3,4-epoxybutylamine. New 4-amino-2- hydroxybutyl synthons for the synthesis of hypusine reagents and (R)-6- and (S)-7-hydroxyspermidine

The synthesis and application of the chiral reagents (R)- and (S)-N- (benzyloxycarbonyl)-3,4-epoxybutylamine is described for the first time. These 4-amino-2-hydroxybutyl synthons are successfully employed in the assembly of two hydroxylated triamines, (R)-6- and (S)-7-hydroxyspermidine, and a previously described hypusine reagent, (2S,9R)-11- [(benzyloxycarbonyl)amino]-7-(benzyloxycarbonyl)-2-[(9- fluorenylmethoxycarbonyl)amino]-9-(tetrahydropyran-2-yloxy)-7-azaundecanoic acid, useful for solution- and solid-phase peptide synthesis. (C) 1999 Elsevier Science Ltd.

Synthesis and Stereochemistry of Hypusine, a New Amino Acid in Bovine Brain

Hypusine, a new basic amino acid occurring in the homogenate of bovine brain tissue, was synthesized to determine the absolute structure.Nα-Benzyloxycarbonyl-L-lysine benzyl ester was coupled with (S)- or (R)-4-benzyloxycarbonylamino-1-bromo-2-butanol derived from L- or D-malic acid, respectively.The products were deprotected by catalytic dehydrogenation.One of the synthetic compounds, i.e., (2S,9R)-2,11-diamino-9-hydroxy-7-azaundecanoic acid, was completely identical with natural hypusine in all respects.