127977-25-7

Upstream product

• 636-98-6 p-nitrobenzene iodide 
• 108957-20-6 (R)-N-(tert-butoxycarbonyl)-3-iodoalanine benzyl ester 
• 59524-02-6 N-tert-butoxycarbonyl-L-serine benzyl ester 
• 100-51-6 benzyl alcohol 
• 94882-74-3 benzyl 2(S)-(tert-butoxycarbonylamino)-3-p-toluenesulfonylpropionate 
• 3695-68-9 L-serine benzyl ester benzenesulfonate salt 
• 24424-99-5 di-tert-butyl dicarbonate 
• 33305-77-0 Boc-Phe(p-NO₂)-OH 
• 100-39-0 benzyl bromide 

Downstream Products

• 184684-98-8 (S)-2-Amino-3-{4-[bis-(2-hydroxy-ethyl)-amino]-phenyl}-propionic acid benzyl ester 
• 850320-89-7 2-{2-[3-bromo-4-(2-tert-butyl-1,1,3-trioxo-1λ⁶-isothiazolidin-5-yl)-phenyl]-1-tert-butoxycarbonylamino-ethyl}-benzoimidazole-1-carboxylic acid tert-butyl ester 
• 850320-88-6 2-{2-[3-bromo-4-(2-tert-butyl-1,1,3-trioxo-2,3-dihydro-1H-1λ⁶-isothiazol-5-yl)-phenyl]-1-tert-butoxycarbonylamino-ethyl}-benzoimidazole-1-carboxylic acid tert-butyl ester 
• 850321-04-9 5-{4-[2-(1H-benzoimidazol-2-yl)-2-(benzothiazol-2-ylamino)-ethyl]-2-bromo-phenyl}-1,1-dioxo-1λ⁶-isothiazolidin-3-one 
• 850320-87-5 2-[2-(3-bromo-4-iodo-phenyl)-1-tert-butoxycarbonylamino-ethyl]-benzoimidazole-1-carboxylic acid tert-butyl ester 
• 929617-80-1 2-[1-tert-butoxycarbonylamino-2-(3-chloro-4-iodo-phenyl)-ethyl]-benzoimidazole-1-carboxylic acid tert-butyl ester 
• 850320-90-0 5-{4-[2-amino-2-(1H-benzoimidazol-2-yl)-ethyl]-2-bromo-phenyl}-2-tert-butyl-1,1-dioxo-1λ⁶-isothiazolidin-3-one 
• 850320-86-4 [1-(1H-benzoimidazol-2-yl)-2-(3-bromo-4-iodo-phenyl)-ethyl]-carbamic acid tert-butyl ester 
• 850315-53-6 3-(4-amino-3-chloro-phenyl)-2-tert-butoxycarbonylamino-propionic acid benzyl ester 
• 929617-84-5 3-(4-amino-3-bromo-phenyl)-2-tert-butoxycarbonylamino-propionic acid benzyl ester 
• 850320-85-3 3-(3-bromo-4-iodo-phenyl)-2-tert-butoxycarbonylamino-propionic acid benzyl ester 
• 850321-49-2 3-(3-bromo-4-iodo-phenyl)-2-tert-butoxycarbonylamino-propionic acid 
• 850322-03-1 2-tert-butoxycarbonylamino-3-(3-chloro-4-iodo-phenyl)-propionic acid 

Relevant academic research and scientific papers

Benzothiazole benzimidazole (S)-isothiazolidinone derivatives as protein tyrosine phosphatase-1B inhibitors

Benzothiazole benzimidazole (S)-isothiazolidinone ((S)-IZD) derivatives 5 were discovered through a peptidomimetic modification of the tripeptide (S)-IZD protein tyrosine phosphatase 1B (PTP1B) inhibitor 1. These derivatives are potent, competitive, and r

Synthesis of α-aminoacyl derivatives of melphalan for use in antibody directed enzyme pro-drug therapy

L-Alanyl-, D-alanyl-, L-prolyl-, L-pyroglutamyl- and D- phenylalanylmelphalan were synthesized in 8 steps, with the reactive nitrogen mustard moiety formed at the penultimate step. After protection of p- nitrophenylalanine with benzyl ester and N-t-butyloxycarbonyl (BOC) groups, the aromatic nitro was reduced to an amine which was reacted with ethylene oxide to give a product with a bis(2-hydroxyethyl)amino moiety. After removal of BOC, it was coupled to the relevant N-benzyloxycarbonyl-α-amino acid. Chlorination of hydroxyethyl yielded the bis(2-chlorethyl)amino compound. Final removal of protecting groups was by catalytic hydrogenolysis.

Synthesis of N-α-aminoacyl derivatives of melphalan for potential use in drug targeting

N-L- and D-alanyl derivatives (9a, 9b) of melphalan (1) have been synthesized in eight steps (9a, 22%; 9b, 18% overall yield) from p-nitro-L-phenylalanine.

Preparation of Enantiomerically Pure Protected 4-Oxo-α-amino Acids and 3-Aryl-α-amino Acids from Serine

The organozinc reagent 13, prepared from the protected β-iodo alanine derivative 3c using ultrasonic activation, is efficiently acylated using acid chlorides in the presence of bis(triphenylphosphine)palladium dichloride to give enantiomerically pure protected 4-oxo-α-amino acids 17 in 39-90percent yield (13 examples).Zinc reagent 13 can also be coupled with aryl iodides in the presence of bis(tri-o-tolylphosphine)palladium dichloride to give enantiomerically pure protected phenylalanine analogues 26, 29, and 30 in 10-67percent yield (11 examples).The reaction tolerates the presence of a variety of functional groups in the acid chloride and the aryl iodide and provides derivatives which can be easily deprotected, at either the carboxyl or amino terminus, to give intermediates suitable for peptide synthesis.

SYNTHESIS OF ENANTIOMERICALLY PURE PROTECTED β-ARYL ALANINES

The organozinc reagent (1), prepared from the β-iodoalanine derivative (2), reacts with aryl iodides at 50 deg C in the presence of catalytic bis(tri-o-tolylphosphine)palladium dichloride to give in moderate to good yields enantiomerically pure protected