29129-67-7

Upstream product

• 116911-14-9 (2S,3S)-3-azido-3-phenyl-propane-1,2-diol 
• 279676-21-0 (+/-)-2-azido-2-phenylacetamide 
• 2935-35-5 (S)-2-phenylglycine 
• 53432-39-6 (R)-1,1,1-trichloro-2-phenylethan-2-ol 
• 113543-39-8 (4S)-3-(2-bromo-1-oxo-2-phenylethyl)-4-(phenylmethyl)-2-oxazolidinone 
• 104266-89-9 (S)-4-benzyl-3-phenylacetyl-2-oxazolidinone 
• 875-74-1 (R)-phenylglycine 
• 111525-67-8 (3(2S),4S)-3-(2-azido-2-phenyl-1-oxoethyl)-4-(phenylmethyl)-2-oxazolidinone 

Downstream Products

• 38329-34-9 (S)-α-amino-α-phenylacetic acid hydrochloride 
• 25705-52-6 (R)-phenylglycine hydrochloride 

Relevant academic research and scientific papers

Triazolopeptides: chirospecific synthesis and cis/trans prolyl ratios of structural isomers

As cis/trans prolyl isomerization plays a crucial role in various biological processes, peptide mimics capable of modifying the cis/trans Xaa-Pro ratio are of particular interest. A practical approach toward proline derived triazolopeptides employing [3+2] azide-alkyne cycloadditions as the key reaction step and the analysis of their cis/trans prolyl ratios are reported. Structural investigations indicated the adjustability of both the cis-percentage and the conformational stability toward intramolecular H-bonding effects.

Improved solid-phase peptide synthesis method utilizing alpha-azide-protected amino acids.

[structure: see text]. Pure alpha-azido acids were prepared using an efficient diazo transfer method followed by buffered workup. These building blocks were used to prepare small peptides on Wang resin by two approaches. Peptides prone to diketopiperazine formation were prepared in good yields by coupling acids to resin bound iminophosphoranes during Fmoc-Wang synthesis. The iminophosphoranes can also be hydrolyzed under neutral conditions to provide unprotected amines ready for further coupling.

A practical asymmetric synthesis of homochiral α-arylglycines

Enantioselective reduction of a series of substituted aryl trichloromethyl ketones with the CBS-catecholborane reagent afforded homochiral aryl trichloromethyl carbinols which have been elaborated to give homochiral α-arylglycines in high e.e.

Enzymatic and chiral HPLC resolution of α-azido acids and amides

For the first time, enzymatic resolution of α-azido acid amides has been successfully demonstrated with high yields and enantiomeric excess. In one case dynamic kinetic resolution was achieved leading to more than 50% yield of the enantiomerically pure azido acid. Chiral HPLC was also used to separate racemic α-azido acids and the separation process was automated. Two routes to enantiopure α-azido acid building blocks for solid-phase peptide synthesis have, therefore, been established. Copyright (C) 2000 Elsevier Science Ltd.

The asymmetric synthesis of α-amino acids. Electrophilic azidation of chiral imide enolates, a practical approach to the synthesis of (R)- and (S)-α-azido carboxylic acids

Two complementary approaches to the asymmetric synthesis of α-amino acids have been achieved. In the initially investigated reaction sequence, the diastereoselective bromination of the illustrated boron enolate with N-bromosuccinimide was followed by stereospecific azide displacement by tetramethylguanidinium azide. The resulting α-azido carboximides may be readily purified to high diastereomeric purity by chromatography on silica. equation presented In the second reaction sequence, the illustrated potassium enolate was treated with 2,4,6-triisopropylbenzenesulfonyl azide, and the intermediate sulfonyl triazene was decomposed through an acetic acid quench to give the α-azido carboximide. The diastereoselection of the reaction as a function of R is as follows: R = Me, CH2Ph, 97:3; R = CHMe2, 98:2; R = CMe3, >99:1; R = Ph, 91:9. The important parameters of this azidation process were evaluated, and experiments were conducted to help elucidate the mechanism of the reaction. equation presented The α-azido carboximide products have been shown to be versatile α-amino acid synthons that may be readily converted to α-amino acids as well as to N-protected α-amino acid derivatives. The racemization-free removal of the chiral auxiliary was achieved in high yield both by saponification and transesterification, either before or after reduction and acylation of the azide functionality.

Regioselective Azide Opening of 2,3-Epoxy Alcohols by : Synthesis of α-Amino Acids

Treatment of 2,3-epoxy alcohols with affords the corresponding 3-azido 1,2-diols, which are readily transformed in two steps to the α-amino acids.