92008-48-5

Upstream product

• 288-32-4 1H-imidazole 
• 2483-49-0 tert-butyloxycarbonyl-L-alanine p-nitrophenyl ester 
• 15761-38-3 L-N-Boc-Ala 
• 530-62-1 1,1'-carbonyldiimidazole 
• 6160-65-2 1,1'-Thiocarbonyldiimidazole 

Downstream Products

• 288-32-4 1H-imidazole 
• 2483-49-0 tert-butyloxycarbonyl-L-alanine p-nitrophenyl ester 
• 69619-23-4 ethyl (S)-4-[(tert-butoxycarbonyl)amino]-3-oxopentanoate 
• 41938-15-2 methyl (tert-butoxycarbonyl)-L-alanyl-L-threoninate 
• 187806-88-8 phenylmethyl (4S)-4-(t-butyloxycarbonyl)amino-3-oxopentanoate 
• 867325-94-8 [(1R)-2-(dimethylphenylsilanyl)-1-methylallyl]-carbamic acid tert-butyl ester 
• 867325-90-4 [(1R)-2-(dimethylphenylsilanyl)-1-methyl-2-oxo-ethyl]-carbamic acid tert-butyl ester 

Relevant academic research and scientific papers

A rapid and efficient one-pot method for the reduction of N-protected α-amino acids to chiral α-amino aldehydes using CDI/DIBAL-H

N-Protected amino acids can be easily converted into chiral α-amino aldehydes in a one-pot reaction by activation with CDI followed by reduction with DIBAL-H. This method delivers Boc-, Cbz- and Fmoc-protected amino aldehydes from proteinogenic amino acids in very good isolated yields and complete stereointegrity.

N-carbamate protected amino acid derived guanidine organocatalysts

We report the preparation of a range of N-protected amino acid derived guanidine organocatalysts and their application to the Michael addition of 2-hydroxy-1,4-napthoquinone to β-nitrostyrene, achieving a maximum ee of 26%. Whilst these catalysts gave poo

COMPOSITIONS CONTAINING, METHODS AND USES OF ANTIBODY-TLR AGONIST CONJUGATES

Disclosed herein are Trastuzumab-linked TLR-agonist derivative analogs that include at least one non-natural amino acid, and methods for making such non-natural amino acids and polypeptides. The Trastuzumab-linked TLR-agonist derivative analogs can includ

Synthesis and preliminary biological evaluations of (+)-isocampholenic acid-derived amides

The synthesis of two novel (+)-isocampholenic acid-derived amines has been realized starting from commercially available (1S)-(+)-10-camphorsulfonic acid. The novel amines as well as (+)-isocampholenic acid have been used as building blocks in the constru

Cu(I)-catalyzed [3+2] cycloadditions of tert-butyl (S)-(3-oxopent-4-yn-2- yl)carbamate to 1-benzylidenepyrazole-3-one-derived azomethine imines

Parallel screening of suitable reaction conditions for Cu(I)-catalyzed [3+2] cycloadditions of (1Z,4R*,5R*)-4- benzoylamino-1-benzylidene-5-phenyl-3-oxopyrazolidin-1-ium-2-ide (1a) to methyl propiolate (2) has established that this reaction proceeds smoothly at room temperature in acetonitrile in the presence of CuI and Huenig's base. The optimized reaction conditions were then applied in regio- and stereo-selective 1,3-dipolar cycloadditions of racemic azomethine imines 1a-e to tert-butyl (S)-(3-oxopent-4-yn-2-yl)carbamate (6) leading to mixtures of diastereomeric non-racemic chromatographically separable cycloadducts 7a-d, 7′ a-d, 8e, and 8′e. The structures of the products were confirmed by NMR spectroscopy.

Process development and pilot-plant synthesis of (S)-tert-butyl 1-oxo-1-(1-(pyridin-2-yl)cyclopropylamino)propan-2-ylcarbamate: Studies on the scale-up of Kulinkovich-Szymoniak cyclopropanation

A practical and scalable synthesis of (S)-tert-butyl 1-oxo-1-(1-(pyridin-2- yl)cyclopropylamino)propan-2-ylcarbamate, an intermediate in the manufacture of a lymphocyte function-associated antigen 1 inhibitor, is described. The titled compound is prepared via an efficient one-pot, two-step telescoped sequence starting from readily available materials. A modified Kulinkovich-Szymoniak cyclopropanation of a nitrile followed by in situ amide formation with an activated carboxylic acid derivative afforded the target product in about 50% overall isolated yield and >97% purity.

Conversion of α-amino acids into bioactive o-aminoalkyl resorcylates and related dihydroxyisoindolinones

The synthesis of biologically active o-aminoalkyl resorcylates and related dihydroxyisoindolinones from functionalized α-amino acids without the use of phenolic protection is described. The key aminoalkyl-diketo-dioxinone intermediates were prepared utilizing a crossed Claisen condensation reaction in the presence of diethylzinc. The aromatic unit was constructed via late stage cyclization and aromatization, and subsequent modification provided the novel resorcylates which showed activity against a selection of receptors and kinases, including 5-HT and CDK.

Carbonyldiimidazole (CDI) mediated synthesis of Nα- protected amino acid azides: Application to the one-pot preparation of ureidopeptides

Synthesis of Nα-protected amino acyl azides starting from corresponding acids via the carbonyldiimidazole (CDI) activation is described. The protocol is extended for a one-pot preparation of ureido peptides that circumvents the isolation of acy

Chirality transfer in the aza-[2,3]-Wittig sigmatropic rearrangement

The aza-[2,3]-Wittig sigmatropic rearrangements of substrates derived from enantiomerically pure alanine, valine and serine with phenyl and ester anion stabilising groups were investigated for their efficiency in chirality transfer. It was found that a me

Inhibitors of biotin biosynthesis as potential herbicides

Isosteric derivatives and analogues of the 7-keto-8-aminopelargonic acid (KAPA), 7,8-diaminopelargonic acid (DAPA) and desthiobiotin (DTB) vitamer intermediates involved in the biosynthetic pathway of biotin were prepared and evaluated as potential herbicides. The most active compound was desmethyl-KAPA which displayed a GR50 (concentration of the active compound that causes a 50% growth inhibition) value of 8 ppm, where values 2 showed moderate activity.