226256-83-3

Upstream product

• 142955-51-9 N-butoxycarbonyl-L-phenylalanine anhydride 
• 4301-14-8 acetylenemagnesium bromide 
• 87694-53-9 Boc-Phe-OH N,O-dimethyl hydroxamate 
• 1066-54-2 trimethylsilylacetylene 
• 13734-34-4 N-tert-butoxycarbonyl-L-phenylalanine 

Downstream Products

• 178894-52-5 (3R,4S)-4-[N-(tert-butoxycarbonyl)amino]-5-phenyl-pent-1-yn-3-ol 
• 161828-21-3 (3S,4S)-4-[N-(tert-butoxycarbonyl)amino]-5-phenyl-pent-1-yn-3-ol 
• 863650-77-5 (S,E)-t-butyl (5-(diethylamino)-3-oxo-1-phenylpent-4-en-2-yl)carbamate 
• 1614240-08-2 methyl (S,Z)-(4-((tert-butoxycarbonyl)amino)-3-oxo-5-phenylpent-1-en-1-yl)glycinate 
• 1614240-09-3 methyl (S,E)-(4-((tert-butoxycarbonyl)amino)-3-oxo-5-phenylpent-1-en-1-yl)glycinate 
• 1614240-12-8 methyl ((S,Z)-4-((tert-butoxycarbonyl)amino)-3-oxo-5-phenylpent-1-en-1-yl)-L-alaninate 
• 1614240-13-9 methyl ((S,E)-4-((tert-butoxycarbonyl)amino)-3-oxo-5-phenylpent-1-en-1-yl)-L-alaninate 
• 1614240-16-2 methyl ((S,Z)-4-((tert-butoxycarbonyl)amino)-3-oxo-5-phenylpent-1-en-1-yl)-L-valinate 
• 1614240-21-9 dimethyl ((S,Z)-4-((tert-butoxycarbonyl)amino)-3-oxo-5-phenylpent-1-en-1-yl)-L-glutamate 
• 1614240-22-0 dimethyl ((S,E)-4-((tert-butoxycarbonyl)amino)-3-oxo-5-phenylpent-1-en-1-yl)-L-glutamate 
• 1614240-25-3 methyl ((S,Z)-4-((tert-butoxycarbonyl)amino)-3-oxo-5-phenylpent-1-en-1-yl)-L-tyrosinate 
• 1614240-26-4 methyl ((S,E)-4-((tert-butoxycarbonyl)amino)-3-oxo-5-phenylpent-1-en-1-yl)-L-tyrosinate 
• 1614240-31-1 methyl ((S,Z)-4-((tert-butoxycarbonyl)amino)-3-oxo-5-phenylpent-1-en-1-yl)-L-phenylalaninate 
• 1614240-32-2 methyl ((S,E)-4-((tert-butoxycarbonyl)amino)-3-oxo-5-phenylpent-1-en-1-yl)-L-phenylalaninate 

Relevant academic research and scientific papers

Synthesis of enaminone-based vinylogous peptides

Vinylogous peptides 3 with a vinyl fragment inserted into the peptide C-N bond were prepared from ynones 6 and enaminones 7 that are easily available from Boc-protected α-amino acids 4. Coupling at the C terminus was achieved by 1,4-addition of amino esters 5 to the C≡C bond in 6 or by substitution of the NMe2 group in 7 to give N-terminal vinylogues 3a-p. Coupling at the N terminus of 3 and 7, in contrast, required temporary protection of the acidolytically labile enamino moiety. Thus, cyclization of 6 or 7 with hydroxylamine, removal of the Boc group with HBr-AcOH, acylation of free amine 10 with BocGlyOH (4a), and hydrogenolytic deprotection of the enamino moiety in the presence of GlyOMe (5a) led to tripeptides 3q-s with vinylogous amide as the central building block. Copyright

Transformation of amino acids into nonracemic 1-(heteroaryl)ethanamines by the enamino ketone methodology

N-Protected L-phenylalanines 1a,b were transformed, via the corresponding Weinreb amides 2 and ethynyl ketones 3, into chiral enamino ketones 4 (Scheme 1). Similarly, L-threonine 6 was transformed in four steps into the enamino ketone 10. Cyclocondensatio

Synthesis of functionalized compounds containing pyridazine and related moieties

3-Aminopyridazines 17 and 3-hydrazinopyridazines 18 were used as building blocks for the preparation of various types of functionalized, pyridazine ring containing compounds. 3-Aminopyridazines were employed in the synthesis of 3-(6-chloroimidazo[1,2-b]py

A synthetic approach to 3-hydroxy 4-substituted carboxylic acids based on the stereoselective reduction of 1-trimethylsilyl-1-alkyn-3-ones

The oxazaborolidine-mediated reduction of chiral, 4-substituted 1-trimethylsilyl-1-alkyn-3-ones followed by hydroboration affords syn or anti 3-hydroxy 4-substituted carboxylic acids, common substructures of a number of biologically active macrolides, peptides and depsipeptides, with high control on the new C(3) stereocenter. This strategy has been applied to the synthesis of (3S,4S)-3-hydroxy-4-methylheptanoic acid and of N-Boc-statine, constituents of permentin A and pepstatin, respectively. (C) 2000 Elsevier Science Ltd.

Diastereoselective synthesis of N-protected β-Amino-α-hydroxyacids (norstatines) from urethane N-carboxyanhydrides (UNCAs)

β-Amino-α-hydroxyacids (norstatines) are prepared from urethane N- protected carboxyanhydrides (UNCAs); the key step is the diastereoselective reduction of a keto-acetylenic compound, which lead is, with syn diastereoselectivity, to the corresponding prop