56877-38-4

Upstream product

• 1492-52-0 methyl (S)-2-(benzyloxycarbonlamino)-3-(p-toluenesulfonyl)propionate 
• 62107-38-4 methyl (R)-(+)-2-(benzyloxycarbonylamino)-3-chloropropionoate 
• 1676-81-9 N-benzyloxycarbonyl-L-serine methyl ester 
• 186581-53-3 diazomethane 
• 1145-80-8 N-(benzyloxycarbonyl)-L-serine 
• 501-53-1 benzyl chloroformate 

Downstream Products

• 21149-17-7 methyl 2-(benzyloxycarbonylamino)acrylate 
• 142993-20-2 (S)-2-Benzyloxycarbonylamino-5-cyano-6-((3aR,4R,6R,6aR)-6-methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-hexanoic acid methyl ester 
• 219635-84-4 (+)-methyl 2-N-benzyloxycarbonylamino-5-carboxamidohex-5-enate 
• 78553-47-6 methyl (2S)-2-[N-(benzyloxycarbonyl)amino]pent-4-enoate 
• 1043926-51-7 N^α-benzyloxycarbonyl-p-[2,3-dihydro-1H-naphtho[1,8-de]-1,3-diaza-2-(10B)borinyl]-L-phenylalanine methyl ester 
• 1017933-24-2 (2S)-2-benzyloxycarbonylamino-4-oxo-5-cyclopropylpentanoic acid methyl ester 
• 1017933-32-2 (2S)-2-benzyloxycarbonylamino-4,4-difluoro-5-cyclopropylpentanoic acid methyl ester 
• 1322744-52-4 (S)-2-benzyloxycarbonylamino-3-[1-(toluene-4-sulfonyl)-1H-indol-3-yl]propionic acid methyl ester 
• 1322744-56-8 (S)-2-benzyloxycarbonylamino-3-[7-chloro-1-(toluene-4-sulfonyl)-1H-indol-3-yl]propionic acid methyl ester 

Relevant academic research and scientific papers

Total Synthesis of Ecumicin

The first total synthesis of the potent anti-mycobacterial cyclic depsipeptide natural product ecumicin is described. Synthesis was achieved via a solid-phase strategy, incorporating the synthetic non-proteinogenic amino acids N-methyl-4-methoxy-l-tryptophan and threo-β-hydroxy-l-phenylalanine into the growing linear peptide chain. The synthesis employed key on-resin esterification and dimethylation steps as well as a final macrolactamization between the unusual N-methyl-4-methoxy-l-tryptophan unit and a bulky N-methyl-l-valine residue. The synthetic natural product possessed potent antimycobacterial activity against the virulent H37Rv strain of Mycobacterium tuberculosis (MIC90 = 312 nM).

CALPAIN MODULATORS AND METHODS OF PRODUCTION AND USE THEREOF

The present technology relates to compounds, kits, compositions, and methods useful for the treatment of fibrotic disease. In some aspects, the present technology provides for treatment of various diseases or disorders associated or mediated, at least in part, by calpains, such as CAPN1, CAPN2, and/or CAPN9. The present technology is generally applicable to compounds which inhibit myofibroblast differentiation.

Synthesis and evaluation of phenylalanine-derived trifluoromethyl ketones for peptide-based oxidation catalysis

We report the synthesis of phenylalanine-derived trifluoromethyl ketones for the in situ generation of dioxiranes for the purpose of oxidation catalysis. The key features of this synthesis include the use of a masked ketone strategy and a Negishi cross-coupling to access the parent amino acid. The derivatives can be readily incorporated into a peptide for use in oxidation chemistry and exhibit good stability and reactivity.

Light-mediated deoxygenation of alcohols with a dimeric gold catalyst

A new protocol for the reductive deoxygenation of primary alcohols was explored. This photo-mediated method combines a novel approach to bromination of alcohols merged with the powerful reducing capability of [Au2(dppm)2]Cl2 [dppm = 1,1-bis(diphenylphosphino)methane] as a photoredox catalyst. The highly efficient methods discussed are marked by the use of UVA light-emitting diodes, which have significantly reduced reaction times and lowered setup cost.

Synthesis of chiral Nβ-protected amino diselenides from the corresponding amino alkyl iodides using NaBH2Se3 as a selenating reagent and their conversion to seleninic acids

A convenient approach has been presented for the synthesis of Nβ-protected amino diselenides from the corresponding amino alkyl iodides using in situ generated NaBH2Se3 as an efficient selenating reagent. All the diselenid

Development of the first and practical method for enantioselective synthesis of 10B-enriched p-borono-l-phenylalanine

At present p-(10B)borono-l-phenylalanine (l-10Bpa) is used clinically as an excellent 10B carrier for BNCT; however, its enantioselective synthesis has not been reported yet. The present Letter describes the first and prac

The discovery of odanacatib (MK-0822), a selective inhibitor of cathepsin K

Odanacatib is a potent, selective, and neutral cathepsin K inhibitor which was developed to address the metabolic liabilities of the Cat K inhibitor L-873724. Substituting P1 and modifying the P2 side chain led to a metabolically robust inhibitor with a long half-life in preclinical species. Odanacatib was more selective in whole cell assays than the published Cat K inhibitors balicatib and relacatib. Evaluation in dermal fibroblast culture showed minimal intracellular collagen accumulation relative to less selective Cat K inhibitors.

Cathepsin cysteine protease inhibitors

This invention relates to a novel class of compounds which are cysteine protease inhibitors, including but not limited to, inhibitors of cathepsins K, L, S and B. These compounds are useful for treating diseases in which inhibition of bone resorption is indicated, such as osteoporosis.

Synthesis of new 3- and 4-substituted analogues of acyl homoserine lactone quorum sensing autoinducers

The quorum sensing mechanism in Gram-negative bacteria uses small intercellular signal molecules, N-acyl-homoserine lactones (AHLs), to control transcription of specific genes in relation to population density. In this communication, we describe the parallel synthesis of new AHL analogues, in which substituents have been introduced into the 3- and 4-positions of the lactone ring. These analogues have been screened for their ability to activate and inhibit a Vibrio fischeri LuxI/LuxR-derived quorum sensing reporter system.

Convenient preparation of (R)- and (S)-1-(2-amino-3-iodo)propanol derivatives from (S)-serine: Application in radical addition reactions

An efficient three step synthesis of the (R)- and (S)-1-(2-amino-3-iodo)propanol derivatives 4 and 7 from (S) serine is proposed. Their use in radical reactions is illustrated.