33985-13-6

Upstream product

• 2749-11-3 (S)-Alaninol 
• 98-88-4 benzoyl chloride 
• 57707-57-0 (S)-2-benzoylamino-1-benzoyloxy-propane 
• 32619-69-5 L-Alanine, N-benzoyl-, ethyl ester 
• 65-85-0 benzoic acid 
• 877-39-4 4-methyl-2-phenyloxazole 
• 1300551-08-9 (R)-4-methyl-2-phenyloxazoline 

Downstream Products

• 157774-53-3 N-<(phenylmethoxy)carbonyl>-D-alanine ethyl ester 
• 157774-52-2 (-)-N-Benzyloxycarbonyl-D-alanyl-N'-benzoyl-L-alaninylester 
• 458560-71-9 (S)-3-benzyl-4-methyl-[1,2,3]-oxathiazolidine-2,2-dioxide 
• 1413930-74-1 (S)-ethyl 5-(benzylamino)hex-2-ynoate 
• 1458696-22-4 (S)-N-(1-hydroxypropan-2-yl)benzothioamide 
• 22906-50-9 (S)-4-methyl-2-phenyl-4,5-dihydrothiazole 
• 1365538-52-8 C₂₄H₃₀N₂O₅ 
• 1365538-48-2 C₂₄H₃₀N₂O₅ 
• 60625-90-3 Cbz-alanine ethyl ester 
• 157774-51-1 (-)-N-Benzyloxycarbonyl-L-alanyl-N'-benzoyl-L-alaninylester 

Relevant academic research and scientific papers

Phosphorus-Based Organocatalysis for the Dehydrative Cyclization of N-(2-Hydroxyethyl)amides into 2-Oxazolines

A metal-free, biomimetic catalytic protocol for the cyclization of N-(2-hydroxyethyl)amides to the corresponding 2-oxazolines (4,5-dihydrooxazoles), promoted by the 1,3,5,2,4,6-triazatriphosphorine (TAP)-derived organocatalyst tris(o-phenylenedioxy)cyclotriphosphazene (TAP-1) has been developed. This approach requires less precatalyst compared to the reported relevant systems, with respect to the phosphorus atom (the maximum turnover number (TON) ～30), and exhibits a broader substrate scope and higher functional-group tolerance, providing the functionalized 2-oxazolines with retention of the configuration at the C(4) stereogenic center of the 2-oxazolines. Widely accessible β-amino alcohols can be used in this approach, and the cyclization of N-(2-hydroxyethyl)amides provides the desired 2-oxazolines in up to 99% yield. The mechanism of the reaction was studied by monitoring the reaction using spectral and analytical methods, whereby an 18O-labeling experiment furnished valuable insights. The initial step involves a stoichiometric reaction between the substrate and TAP-1, which leads to the in situ generation of the catalyst, a catechol cyclic phosphate, as well as to a pyrocatechol phosphate and two possible active intermediates. The dehydrative cyclization was also successfully conducted on the gram scale.

Weak coordinated nitrogen functionality enabled regioselective C-H alkynylationviaPd(ii)/mono-N-protected amino acid catalysis

The exploration of weak coordinated amine derivative enabled regioselective C-H functionalization remains challenging due to the elusive achievement of reactivity and selectivity simultaneously. Herein, regioselective C-H alkynylation of various readily transformable nitrogen functionalities was developed with great efficiency, with the assistance of the mono-N-protected amino acid (MPAA) ligandviaPd(ii) catalysis proceedingvia5, 6 and 7-membered palladacycle intermediates.

Microwave-Assisted Synthesis of 2-Substituted 2-Thiazolines and 5,6-Dihydro-4 H -1,3-thiazines

An efficient and general method for the synthesis of 2-substituted thiazolines and 5,6-dihydro-4 H -1,3-thiazines is developed via microwave-assisted ring closure of ω-thioamidoalcohols promoted by ethyl polyphosphate (PPE). The cyclization reaction involves an S N 2-type mechanism and features the advantages of very short reaction times, high yields and a predictable stereochemical outcome. The acyclic precursors are prepared in high overall yields by an improved diacylation-thionation-saponification sequence from commercially available ω-amino alcohols. The whole process is metal-free and operationally simple.

Microwave-Assisted Synthesis of 2-Aryl-2-oxazolines, 5,6-Dihydro-4H-1,3-oxazines, and 4,5,6,7-Tetrahydro-1,3-oxazepines

The first general procedure for the synthesis of 5- to 7-membered cyclic iminoethers by microwave-assisted cyclization of ω-amido alcohols promoted by polyphosphoric acid (PPA) esters is presented. 2-Aryl-2-oxazolines and 5,6-dihydro-4H-1,3-oxazines were efficiently prepared using ethyl polyphosphate/CHCl3. Trimethylsilyl polyphosphate in solvent-free conditions allowed for the synthesis of hitherto-unreported 4,5,6,7-tetrahydro-1,3-oxazepines. The method involves good to excellent yields and short reaction times.The reaction mechanism and the role of PPA esters were investigated in a chiral substrate.

Synthesis and in vitro antitumor activity of asperphenamate derivatives as autophagy inducer

In an effort to improve the aqueous solubility and the antitumor activity of natural product asperphenamate, we have designed and synthesized three series of asperphenamate derivatives, including series I (simplifying molecular skeleton series), series II (introducing a hydroxyl group to A-phenyl ring series) and series III (disrupting molecular planarity series). All derivatives have displayed a significantly increased solubility compared with asperphenamate. Their growth inhibitory activities in vitro were screened by the standard MTT method in MCF-7, HeLa, and BEL-7402 cell lines. With the exception of the derivatives in series I, most of derivatives in series II and series III showed growth inhibitory activity. Among all derivatives, IM23b in series III showed the greatest potency in human breast cancer MCF-7 cells. The cellular potency of IM23b was approximately 1.5-fold more potent than that of cisplatin. The mechanism of cell death induced by IM23b in human breast cancer MCF-7 cells was further investigated. We concluded that the cell death was induced by autophagy instead of apoptosis or cell cycle arrest.

A [3+3] cyclization strategy for asymmetric synthesis of alkyl substituted piperidine-2-ones using 1,2-cyclic sulfamidates: A formal synthesis of (S)-coniine from l-norvaline

Regioselective ring-opening reactions of a set of representative 1,2-cyclic sulfamidates with lithium triethylorthopropiolate proceeded efficiently to deliver the corresponding δ-amino-α,β-unsaturated esters after acidic hydrolysis. Hydrogenation of the unsaturated esters and subsequent thermal cyclization afforded the related alkyl substituted piperidine-2-ones. This approach represents a novel [3+3] cyclization strategy for the asymmetric synthesis of alkyl substituted piperidin-2-ones. Efficiency of the cyclization process is illustrated by a formal asymmetric synthesis of (S)-coniine from l-norvaline.

Catalytic asymmetric hydrogenation of N-Boc-imidazoles and oxazoles

Substituted imidazoles and oxazoles were respectively hydrogenated into the corresponding chiral imidazolines and oxazolines (up to 99% ee). The highly enantioselective hydrogenation was achieved by using the chiral ruthenium catalyst, which is generated

Synthesis and Spectroscopic Properties of the Stereoisomeric Esters from L- and D-N-Benzoylalanin and L- and D-N-Benzoylalaninol

The synthesis of the stereoisomeric esters of L- and D-N-benzoylalanine and L- and D-N-benzoylalaninol is described. - Keywords: N-Benzoylalaninyl-N'-benzoylalaninate, Stereoisomeric Esters, 1H NMR Data, 13C NMR Data, CD Data