182880-90-6

Upstream product

• 773-64-8 2-mesitylenesulphonyl chloride 
• 3182-95-4 L-Phenylalaninol 
• 178380-05-7 C₁₈H₂₁NO₄S 
• 1039025-10-9 N-(2,4,6-trimethylbenzenesulfonyl)-L-phenylalanine methyl ester 

Downstream Products

• 1032477-19-2 2,2'-diacetoxy-3,3'-bis[(2S,4S)-4-benzyl-3-(2,4,6-trimethylbenzenesulfonyl)-1,3-oxazolidinyl]-5,5'-di-tert-butyl-biphenyl 
• 1039025-15-4 N-[(1S)-1-methanesulfonylmethyl-2-phenylethyl]-2,4,6-trimethylbenzenesulfonamide 
• 220306-86-5 Methanesulfonic acid (E)-(S)-5-phenyl-4-(2,4,6-trimethyl-benzenesulfonylamino)-pent-2-enyl ester 
• 220306-82-1 Carbonic acid methyl ester (E)-(S)-5-phenyl-4-(2,4,6-trimethyl-benzenesulfonylamino)-pent-2-enyl ester 
• 220306-74-1 (E)-(S)-5-Phenyl-4-(2,4,6-trimethyl-benzenesulfonylamino)-pent-2-enoic acid methyl ester 
• 220306-78-5 N-((E)-(S)-1-Benzyl-4-hydroxy-but-2-enyl)-2,4,6-trimethyl-benzenesulfonamide 
• 187532-00-9 (2S,3S)-3-benzyl-N-(2,4,6-trimethylbenzensulfonyl)-2-vinylaziridine 
• 187531-99-3 (2R,3S)-3-benzyl-N-(2,4,6-trimethylbenzensulfonyl)-2-vinylaziridine 
• 678166-38-6 (4S,2E)-O-methoxycarbonyl-2-methyl-5-phenyl-4-[N-(2,4,6-trimethylphenylsulfonyl)amino]pent-2-en-1-ol 
• 678166-52-4 (4S,2E)-2-methyl-5-phenyl-4-[N-(2,4,6-trimethylphenylsulfonyl)amino]-O-methylsulfonylpent-2-en-1-ol 
• 678166-27-3 methyl (4S,2E)-2-methyl-5-phenyl-4-[N-(2,4,6-trimethylphenylsulfonyl)amino]pent-2-enoate 
• 678166-33-1 (4S,2E)-2-methyl-5-phenyl-4-[N-(2,4,6-trimethylphenylsulfonyl)amino]pent-2-en-1-ol 
• 220324-31-2 N-((S)-1-Formyl-2-phenyl-ethyl)-2,4,6-trimethyl-benzenesulfonamide 

Relevant academic research and scientific papers

Synthesis of a β-tetrapeptide analog as a mother compound for the development of matrix metalloproteinase-2-imaging agents

Matrix metalloproteinase-2 (MMP-2) is an attractive target for the diagnosis of cancer and atherosclerosis in nuclear imaging. A cyclic decapeptide, cCTTHWGFTLC (cCTT), has been used as the mother compound for the development of MMP-2-imaging agents with high potency and selectivity. Most of radiolabeled derivatives of cCTT currently developed for in vivo studies of MMP-2, however, suffer from low accumulation in the target tissues, such as tumors. For enhanced in vivo stability and tissue penetration, we designed a linear β-tetrapeptide analog, H-β3-Phe-β-Ala- β3-Trp-β3-His-OH (1), to mimic cCTT. The component β-amino acids were prepared by reduction of N-protected α-amino acid methyl esters to the alcohols, followed by conversion into the cyanides, and subsequent hydrolysis. Compound 1 was obtained from these β-amino acids by the conventional solution method. In MMP-2 inhibition assay, compound 1 displayed desirably significant inhibition, which was comparable to cCTT. These findings suggest that compound 1 may serve as a mother compound in the design and development of in vivo MMP-2-imaging agents.

Asymmetric Strecker reaction of N-benzhydrylimines utilising new tropos biphenyldiol-based ligands

The synthesis of a library of N-arenesulfonyl-1,3-oxazolidinyl-substituted biphenyldiols is presented. A set of two central intermediates together with easily accessible N-arenesulfonylamino alcohols furnish a broad variety of 1,3-oxazolidines. These are applied as chiral tropos ligands in a titanium-mediated Strecker-type reaction of N-benzhydrylimines. A correlation between the ee values in the product and the diastereomeric ratio concerning the chiral axis of the ligand is made. Those substituents in the ligand which proved to lead to a higher preference for one diastereomeric conformer of the chiral axis in related compounds now provide the most selective ligands. Two privileged ligands are identified that afford superior results in 8 of 13 screenings. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.

Efficient synthesis of new chiral 1,2-benzothiazin-3-one 1,1-dioxide derivatives via lateral lithiation of 3-N-mesitylenesulfonyl-1,3-oxazolidin-2-ones

Chiral 3-N-mesitylenesulfonyl-1,3-oxazolidin-2-ones 4a-e derived from (l)- and (d)-amino acids 1a-e undergo lateral lithiation with lithium diisopropylamide and TMEDA in anhydrous THF to provide new optically-active 1,2-benzothiazin-3-one 1,1-dioxide deri

A 2,3-cis-selective synthesis of aziridines bearing a vinyl group from allyl methyl carbonates and allyl mesylates

A convenient method for the synthesis of synthetically useful chiral 2-vinylaziridines from natural α-amino acids is described. Satisfactory 2,3-cis-selectivities are obtained by exposure of methyl carbonates of various allylic alcohols bearing an N-protected amino group to a catalytic amount of tetrakis(triphenylphosphine)palladium(0), Pd(PPh3)4, in aprotic solvents such as THF. Base-promoted aziridination of mesylates of various N-protected amino allylic alcohols followed by Pd(PPh3)4 catalyzed isomerization for the 2,3-cis-selective synthesis of vinylaziridines is also presented.

Catalysis with inorganic cations. VI. The effect of chiral bis-oxazoline-magnesium perchlorate catalysts on chemo- and enantioselectivity of intramolecular Hetero Diels-Alder and ene reaction

(E)1-acetyl-[2-(3-methyl-2-butenyloxy)benzylidene]indolin-2-one (1) gives competition between the intramolecular Hetero Diels-Alder (HDA) (thermal conditions) and the intramolecular ene reaction (IER) (magnesium perchlorate - MP - catalyzed conditions). Several complexes derived from MP and chiral bis-oxazolines were found to be excellent chemo- and enantioselective catalysts with a different degree of selectivity depending on the substituents on the oxazoline ring. The most chemoselective oxazolinic ligand forced the reaction to give a ratio of [HDA]:[[IER] products 5:95. The trans-(4,5-diphenyloxazoline)-MP complex is the best enantioselective catalyst and the product of the IER of 1 can be prepared in 75% yield and 88% e.e..