55044-06-9

Usage

Uses

Used in Pharmaceutical Industry:
2-Phenyloxazoline-4-carboxylic acid methyl ester is used as an intermediate for the synthesis of (S)-Valiolamine Voglibose, which is the main S-enantiomeric intermediate of Voglibose (V750000). Voglibose is an α-glucosidase inhibitor that helps in managing postprandial hyperglycemia and hyperinsulinemia by delaying the digestion and absorption of carbohydrates.

Upstream product

• 5680-80-8 methyl (2S)-2-amino-3-hydroxypropanoate hydrochloride 
• 825-60-5 benzimidic acid ethyl ester 
• 2104-89-4 Ser-OMe 
• 5333-86-8 ethyl benzimidate hydrochloride 
• 2788-84-3 (S)-serine methyl ester 
• 5619-04-5 methyl 2-amino-3-hydroxypropanoate hydrochloride 
• 932-90-1 Benzaldoxime 
• 100-47-0 benzonitrile 
• 100-52-7 benzaldehyde 
• 59171-72-1 2-phenyl-oxazole-4-carboxylic acid methyl ester 
• 1137241-59-8 N-benzoyl-O-tritylserine methyl ester 
• 5873-90-5 methyl benzimidate hydrochloride 
• 20989-42-8 N-benzoylserine methyl ester 
• 50-00-0 formaldehyd 

Downstream Products

• 25755-94-6 methyl 2,5-diphenyloxazole-4-carboxylate 
• 1370731-50-2 C₂₂H₁₆N₂O₆ 
• 1370731-61-5 methyl 2-phenyl-5-(4-methylphenyl)oxazole-4-carboxylate 
• 1370731-62-6 methyl 2-phenyl-5-(3-methylphenyl)oxazole-4-carboxylate 
• 1370731-67-1 methyl 2-phenyl-5-(3,4-dichlorophenyl)oxazole-4-carboxylate 
• 1370731-68-2 methyl 2-phenyl-5-(2,3-dichlorophenyl)oxazole-4-carboxylate 
• 1370731-73-9 methyl 2-phenyl-5-(2,5-dimethylphenyl)oxazole-4-carboxylate 
• 1370731-75-1 methyl 2-phenyl-5-(3-nitrophenyl)oxazole-4-carboxylate 
• 1370731-78-4 C₁₇H₈⁽²⁾H₅NO₃ 
• 92-71-7 2,5-diphenyloxazole 
• 2549-35-1 2,5-diphenyl-4-hydroxymethyloxazole 
• 1613449-98-1 tert-butyl 2-(benzylamino)-2-(hydroxymethyl)butanoate 
• 1613450-04-6 tert-butyl 2-(benzylamino)-2-(hydroxymethyl)pentanoate 
• 1613450-05-7 tert-butyl 2-benzyl-2-(benzylamino)-3-hydroxypropanoate 

Relevant academic research and scientific papers

I2-Catalyzed C-O Bond Formation and Dehydrogenation: Facile Synthesis of Oxazolines and Oxazoles Controlled by Bases

A general method for the synthesis of oxazolines and oxazoles was developed through I2-catalyzed C-O bond formation and dehydrogenation with the same oxidant, TBHP. By simply tuning reaction bases, either oxazolines or oxazoles were selectively

Synthesis of protected α-alkyl lanthionine derivatives

Protected α-alkyl lanthionine derivatives were synthesized in five steps starting from a known phenyloxazoline precursor. This approach involved the synthesis of a family of substituted cyclic sulfamidates and their regioselective opening by nucleophilic attack with a protected cysteine. This efficient multistep strategy affords various α-alkylated lanthionine derivatives in high yields.

Pd(ii)-catalyzed direct C5-arylation of azole-4-carboxylates through double C-H bond cleavage

The first palladium-catalyzed direct C5-arylation of azole-4-carboxylates with simple unactivated arenes through double C-H bond cleavage is realized. This protocol provided a straightforward access to diverse 5-arylsubstituted azole-4-carboxylic derivatives with good functional group tolerance. The Royal Society of Chemistry 2012.

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

COMPOUNDS FOR TREATMENT OF CANCER

The present invention relates to novel compounds having anti-cancer activity, methods of making these compounds, and their use for treating cancer and drug-resistant tumors, e.g. melanoma, metastatic melanoma, drug resistant melanoma, prostate cancer and drug resistant prostate cancer.

The use of phosphonium anhydrides for the synthesis of 2-oxazolines, 2-thiazolines and 2-dihydrooxazine under mild conditions

β-Hydroxy amides 6 and 7 were treated with triphenylphosphonium anhydride trifluoromethane sulfonate (3), or the cyclic analogue 4, to generate 2-oxazolines 5 and 8 under mild conditions. The reaction was optimised by examining the number of equivalents of reagents 3 or 4, or diisopropylethyl amine required to best effect cyclisation. The effects of altering the reaction temperature, reaction time, concentration, solvent, and addition rate also were investigated. However, it was found that use of a trityl group to block reaction at the hydroxyl or thiol group of the starting amides, and subsequent in situ detritylation, in the absence of base, led to greatly improved yields. Reagent 4 offered significant advantages in the purification of products and was used to dehydrate a range of trityl derivatives to form simple oxazolines, thiazolines, and a dihydro-1,3-oxazine, in high yield (85-99%), as well as a tetrahydro-1,3-oxazepine (31%).

Solid-phase synthesis of α-alkylserines via phase-transfer catalytic alkylation of polymer-supported 2-phenyl-2-oxazoline-4-carboxylate

Described is the development of a new solid-phase synthetic method for α-alkylserines in which phase-transfer catalytic alkylation of polymer-supported 2-phenyl-2-oxazoline-4-carboxylate (12) is the key step. The easy preparation of the polymer-supported

A flexible synthetic approach to the hennoxazoles

Three advanced intermediates corresponding to the carbon skeleton of the hennoxazoles have been prepared. Central to the strategy is the synthesis of the oxazoles prior to coupling with the other fragments and a dithiane addition to allow for the generati

Synthesis of functionalized oxazolines and oxazoles with DAST and Deoxo-Fluor.

[formula: see text] A mild and highly efficient cyclization of beta-hydroxy amides to oxazolines is described using DAST and Deoxo-Fluor reagents. A one-pot protocol for the synthesis of oxazoles from beta-hydroxy amides is also presented.