488727-73-7

Upstream product

• 108-86-1 bromobenzene 
• 1377320-83-6 (R)-4-[(S)-hydroxy(phenyl)methyl]-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester 
• 95715-87-0 (R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine 
• 488727-71-5 (4R)-(1-hydroxy-phenyl-methyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester 

Downstream Products

• 1377320-83-6 (R)-4-[(R)-hydroxy(phenyl)methyl]-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester 
• 1377320-83-6 (R)-4-[(S)-hydroxy(phenyl)methyl]-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester 
• 1294479-62-1 tert-butyl ((1S,2R)-1,3-dihydroxy-1-phenylpropan-2-yl)-carbamate 
• 32946-42-2 (2S,3S)-2-amino-3-hydroxy-3-phenylpropanoic acid 
• 487060-72-0 (2S,3S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-hydroxy-3-phenylpropanoic acid 
• 488727-87-3 ((((1S)-allyl-(2,2,2-trifluoro-acetyl)-amino)-methyl)-2-phenyl-allyl)-carbamic acid tert-butyl ester 
• 488727-83-9 toluene-4-sulfonic acid (2S)-tert-butoxycarbonylamino-3-phenyl-but-3-enyl ester 
• 488727-99-7 1-(2,2,2-trifluoro-acetyl)-(3S)-tert-butoxycarbonyl-amino-(4S)-phenyl-piperidine 
• 488728-00-3 1-(2,2,2-trifluoro-acetyl)-(3S)-tert-butoxycarbonyl-amino-(4R)-phenyl-piperidine 
• 488727-93-1 1-(2,2,2-trifluoro-acetyl)-(3S)-tert-butoxycarbonyl-amino-4-phenyl-1,2,3,6-tetrahydro-pyridine 
• 488727-79-3 ((1S)-hydroxymethyl-2-phenyl-allyl)-carbamic acid tert-butyl ester 
• 488727-76-0 2,2-dimethyl-(4S)-(1-phenyl-vinyl)-oxazolidine-3-carboxylic acid tert-butyl ester 

Relevant academic research and scientific papers

Total Synthesis of Glycosylated Human Interferon-γ

Interferon-γ(IFN-γ) is a glycoprotein that is responsible for orchestrating numerous critical immune induction and modulation processes and is used clinically for the treatment of a number of diseases. Herein, we describe the total chemical synthesis of homogeneously glycosylated variants of human IFN-γusing a tandem diselenide-selenoester ligation-deselenization strategy in the C- to N-terminal direction. The synthetic glycoproteins were successfully folded, and the structures and antiviral functions were assessed.

Synthetic Studies Toward the Skyllamycins: Total Synthesis and Generation of Simplified Analogues

Herein, we report our synthetic studies toward the skyllamycins, a highly modified class of nonribosomal peptide natural products which contain a number of interesting structural features, including the extremely rare α-OH-glycine residue. Before embarking on the synthesis of the natural products, we prepared four structurally simpler analogues. Access to both the analogues and the natural products first required the synthesis of a number of nonproteinogenic amino acids, including three β-OH amino acids that were accessed from the convenient chiral precursor Garner's aldehyde. Following the preparation of the suitably protected nonproteinogenic amino acids, the skyllamycin analogues were assembled using a solid-phase synthetic route followed by a final stage solution-phase cyclization reaction. To access the natural products (skyllamycins A-C) the synthetic route used for the analogues was modified. Specifically, linear peptide precursors containing a C-terminal amide were synthesized via solid-phase peptide synthesis. After cleavage from the resin the N-terminal serine residue was oxidatively cleaved to a glyoxyamide moiety. The target natural products, skyllamycins A-C, were successfully prepared via a final step cyclization with concomitant formation of the unusual α-OH-glycine residue. Purification and spectroscopic comparison to the authentic isolated material confirmed the identity of the synthetic natural products.

Total Synthesis of Skyllamycins A–C

The skyllamycins are a family of highly functionalized non-ribosomal cyclic depsipeptide natural products which contain the extremely rare α-OH-glycine functionality. Herein the first total synthesis of skyllamycins A–C is reported, together with the biofilm inhibitory activity of the natural products. Linear peptide precursors for each natural product were prepared through an efficient solid-phase route incorporating a number of synthetic modified amino acids. A novel macrocyclization step between a C-terminal amide and an N-terminal glyoxylamide moiety served as a key transformation to install the unique α-OH-glycine unit and generate the natural products in the final step of the synthesis.

Synthesis of β-Thiol Phenylalanine for Applications in One-Pot Ligation-Desulfurization Chemistry

(Chemical Equation Presented) The efficient synthesis of a β-thiol phenylalanine derivative is described starting from Garner's aldehyde. The utility of this amino acid in peptide ligation-desulfurization chemistry is described, including the trifluoroethanethiol (TFET)-promoted one-pot assembly of the 62 residue peptide hormone augurin.

Synthesis and utility of β-selenol-phenylalanine for native chemical ligation-deselenization chemistry

An efficient synthetic route to a suitably protected β-selenol- phenylalanine derivative from commercially available Garner's aldehyde is described. The incorporation of this building block into peptides and its application in native chemical ligation reactions with peptide thioesters are demonstrated. Ligation products were chemoselectively deselenized (including in the presence of unprotected cysteine residues) to provide native peptides.

Synthesis of trans-(3S)-Amino-(4R)-alkyl- and -(4S)-Aryl-piperidines via Ring-Closing Metathesis Reaction

(Matrix Presented) trans-(3S)-Amino piperidines bearing various alkyl and aryl substituents at the C-4 position were synthesized via a ring-closing metathesis reaction. The absolute stereochemistry was controlled using a protected D-serine as a starting material. Stereoselective hydrogenation of allylamines provided trans-(3S)-amino-(4R)-alkyl- and -(4S)-aryl-piperidines. This procedure presents the first method for the asymmetric synthesis of 4-substituted 3-amino piperidines.