133010-22-7

Upstream product

• 52641-32-4 N-benzyloxycarbonyl-L-phenylalanyl chloride 
• 1161-13-3 N-Cbz-L-Phe 

Downstream Products

• 28944-94-7 (S)-methyl 2-((S)-2-(((benzyloxy)carbonyl)amino)-3-phenylpropanamido)propanoate 
• 366498-37-5 (3S,5S)-N-(Cbz-Phe)-3-phenyl-5-(2-methyl-1-propenyl)-L-proline methyl ester 
• 1030600-33-9 6-({[2-(benzyloxycarbonyl)ethyl](tert-butoxycarbonyl)amino}methyl)-2-isopropoxy-3-methoxyphenyl 2-(benzyloxycarbonylamino)-3-phenylpropionate 
• 1030600-36-2 benzyl 4-[{2-[2-(benzyloxycarbonylamino)-3-phenylpropionyloxy]-3-isopropoxy-4-methoxybenzyl}(tert-butoxycarbonyl)amino]butyrate 
• 1030600-38-4 5-benzyl 1-methyl 2-[{2-[2-(benzyloxycarbonylamino)-3-phenylpropionyloxy]-3-isopropoxy-4-methoxybenzyl}(tert-butoxycarbonyl)amino]pentanedioate 
• 244228-14-6 C₃₃H₄₅N₃O₈ 
• 244228-13-5 C₂₅H₃₉N₃O₅ 
• 439589-27-2 (S)-2-Benzyl-1-(4-methoxy-benzyl)-4-oxo-azetidine-2-carboxylic acid (1R,2S,4S)-1-[(dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester 
• 439589-19-2 (S)-2-[(2-Chloro-acetyl)-(4-methoxy-benzyl)-amino]-3-phenyl-propionic acid (1R,2S,4S)-1-[(dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester 
• 439589-16-9 (S)-2-(4-Methoxy-benzylamino)-3-phenyl-propionic acid (1R,2S,4S)-1-[(dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester 
• 439589-31-8 (S)-2-Benzyl-1-(4-methoxy-benzyl)-4-oxo-azetidine-2-carboxylic acid 

Relevant academic research and scientific papers

Direct Synthesis of Acyl Fluorides from Carboxylic Acids with the Bench-Stable Solid Reagent (Me4N)SCF3

A convenient, highly efficient, and selective transformation of aliphatic and aromatic carboxylic acids to acyl fluorides is reported. In contrast to established approaches that require toxic or volatile additives and base and reaction control (i.e., cool

Rapid and column-free syntheses of acyl fluorides and peptides usingex situgenerated thionyl fluoride

Thionyl fluoride (SOF2) was first isolated in 1896, but there have been less than 10 subsequent reports of its use as a reagent for organic synthesis. This is partly due to a lack of facile, lab-scale methods for its generation. Herein we report a novel protocol for theex situgeneration of SOF2and subsequent demonstration of its ability to access both aliphatic and aromatic acyl fluorides in 55-98% isolated yields under mild conditions and short reaction times. We further demonstrate its aptitude in amino acid couplings, with a one-pot, column-free strategy that affords the corresponding dipeptides in 65-97% isolated yields with minimal to no epimerization. The broad scope allows for a wide range of protecting groups and both natural and unnatural amino acids. Finally, we demonstrated that this new method can be used in sequential liquid phase peptide synthesis (LPPS) to afford tri-, tetra-, penta-, and decapeptides in 14-88% yields without the need for column chromatography. We also demonstrated that this new method is amenable to solid phase peptide synthesis (SPPS), affording di- and pentapeptides in 80-98% yields.

PEPTIDE TURN MIMETICS

Peptide mimetics of structure X herein which (i) provide a wide range of sidechain functions at all sidechain positions, (ii) can be incorporated in a peptide sequence, (iii) can be readily synthesized and (iv) have a variety of conformations. There is also provided a novel process which can provide valuable intermediates in relation to production of peptide mimetics of structure X which intermediates have a high degree of chemo- and stereo-selectivity. Preferred mimetics include structures I, II, III, IV, V and VI.

A convenient, one-pot procedure for the preparation of acyl and sulfonyl fluorides using Cl3CCN, Ph3P, and TBAF(t -BuOH) 4

Various carboxylic acids were converted into acyl fluorides in excellent yields by treatment with trichloroacetonitrile, triphenylphosphine, and TBAF(t-BuOH)4 at room temperature. The reaction was applicable to the preparation of acid-sensitive amino acid fluorides without deprotection or rearrangement

Synthesis of Boc- and Z-protected amino acid fluorides employing DAST as a fluorinating agent

DAST [(diethylamino)sulphur trifluoride] has been used as a fluorinating agent for the synthesis of Boc- and Z-protected amino acid fluorides. All the compounds made have been isolated as crystalline solids in good yield and purity.

Amino acid fluorides: Their preparation and use in peptide synthesis

Z or Fmoc amino acid fluorides have been prepared from the protected amino acids and cyanuric fluoride, and have been tested both in the condensation with simple amino acid esters and in Solid Phase Peptide Synthesis.

tert-Butyloxycarbonyl and Benzyloxycarbonyl Amino Acid Fluorides. New, Stable Rapid-Acting Acylating Agents for Peptide Synthesis

A new class of rapid-acting acylating agents, α-BOC and Z amino acid fluorides are obtained as stable, often crystalline, compounds by treatment of the protected amino acid cyanuric fluoride.