111047-54-2

Usage

Uses

Used in Pharmaceutical Industry:
METHYL N-P-TOLUENESULFONYL-L-2-PHENYLGLYCINATE is used as a chemical intermediate for the production of various drugs, leveraging its chiral nature to facilitate the synthesis of pharmaceuticals with specific biological activities.
Used in Agrochemical Industry:
METHYL N-P-TOLUENESULFONYL-L-2-PHENYLGLYCINATE is used as a precursor in the synthesis of agrochemicals, contributing to the development of products with targeted effects in agricultural applications.
Used in Chiral Drug Synthesis:
METHYL N-P-TOLUENESULFONYL-L-2-PHENYLGLYCINATE is used as a key building block in the synthesis of chiral drugs, enabling the creation of pharmaceuticals with enhanced selectivity and efficacy due to its chiral properties.
Used in Biologically Active Molecule Synthesis:
METHYL N-P-TOLUENESULFONYL-L-2-PHENYLGLYCINATE is used as a component in the synthesis of biologically active molecules, allowing for the development of compounds with specific interactions and effects within biological systems.

InChI:InChI=1/C16H17NO4S/c1-12-8-10-14(11-9-12)22(19,20)17-15(16(18)21-2)13-6-4-3-5-7-13/h3-11,15,17H,1-2H3/t15-/m0/s1

Upstream product

• 70-55-3 toluene-4-sulfonamide 
• 55962-05-5 [N-(p-tolylsulfonyl)imino]phenyliodinane 
• 40195-27-5 (1-methoxy-2-phenylvinyloxy)trimethylsilane 
• 15206-55-0 methyl 2-oxo-2-phenylacetate 
• 22979-35-7 Methyl phenyldiazoacetate 
• 98-59-9 p-toluenesulfonyl chloride 
• 350479-90-2 (S,E)-N-benzylidene-4-methylbenzenesulfinamide 
• 111524-98-2 (2S)-2-phenyl-2-(tosylamino)acetic acid 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 19883-41-1 D-phenylglycine methyl ester hydrochloride 
• 922-68-9 Methyl glyoxylate 
• 98-80-6 phenylboronic acid 
• 124-38-9 carbon dioxide 
• 100-52-7 benzaldehyde 

Downstream Products

• 335150-99-7 N-(2-hydroxy-1-phenyl-2-vinyl-but-3-enyl)-4-methyl-benzenesulfonamide 
• 620627-47-6 (2S,4R)-5,5-dimethyl-4-phenyl-N-tosyl-1,2,3-oxathiazolidine 2-oxide 
• 1310105-98-6 C₂₁H₂₉NO₄S₂ 
• 1310105-60-2 C₃₂H₄₃NO₄S₂ 
• 247089-85-6 (R)-p-toluenesulfinamide 
• 620627-46-5 C₁₇H₂₁NO₃S 
• 1384465-75-1 methyl (+/-)-2-phenyl-1-tosylazetidine-2-carboxylate 
• 64-04-0 phenethylamine 
• 24395-14-0 (R)-2-phenyl-N-tosylaziridine 
• 5450-75-9 4-methyl-N-(2-phenylethyl)benzenesulfonamide 

Relevant academic research and scientific papers

Diiodine-Triethylsilane System: Reduction of N-Sulfonyl Aldimines to N-Alkylsulfonamides

Because molecular iodine and hydrosilanes are stable to both air and moisture, reactions using these reagents are easy to operate and require mild reaction conditions. Molecular iodine and a hydrosilane were used to reduce N-sulfonyl aldimines to the corr

Blue light-promoted N–H insertion of amides, isatins, sulfonamides and imides into aryldiazoacetates: Synthesis of unnatural α-aryl amino acid derivatives

A photochemical protocol using blue light allows the N–H insertion of amides, isatins, sulfonamides and imides into aryldiazoacetates to afford the corresponding α-amino esters. This method is experimentally simple, inexpensive and tolerates numerous functional groups, thus allowing the straightforward preparation of a variety of α-aryl amino acid derivatives in good yields.

Additions of Carbohydrate-Derived Alkoxyallenes to Imines and Subsequent Reactions to Enantiopure 2,5-Dihydropyrrole Derivatives

The additions of six alkoxyallenes bearing carbohydrate-derived chiral auxiliaries to imines were systematically studied. The reactions of three lithiated 1-alkoxypropa-1,2-dienes with an N-tosyl imine revealed that the diacetone fructose-derived auxiliary provided the highest diastereoselectivity of 91:9. The preferred absolute configuration of the newly formed stereogenic center was determined by subsequent ozonolysis of the allene moiety, transesterification and comparison with literature data. The analogous reactions of three axially chiral 3-nonyl-substituted 1-alkoxyallenes with these auxiliaries confirm these results and also prove that the configuration of the generated stereogenic center was only steered by the auxiliaries, whereas the chiral axis has essentially no influence. In general, four diastereomers were obtained in various portions, depending on the ratio of the two precursor allene diastereomers and on the auxiliary employed. The obtained dia?-stereomeric allenyl amines were cyclized under different conditions. As expected, under basic conditions, a stereospecific cyclization occurred, whereas under silver nitrate catalysis partial isomerization at the allene stage was observed. Under both conditions the 2,5-cis-disubstituted dihydropyrroles were formed faster than the trans-isomers. Several of the 2-substituted or 2,5-disubstituted dihydropyrrole derivatives could be isolated in diastereomerically pure form and were subsequently converted into the expected pyrrolidin-3-ones by removal of the carbohydrate-derived auxiliary under acidic conditions. The desired products were obtained in good yield and with high enantiopurity. They are suitable starting materials for the synthesis of enantiopure pyrrolidine natural products.

Pd(OAc)2-Catalyzed Asymmetric Hydrogenation of α-Iminoesters

An efficient Pd(OAc)2-catalyzed asymmetric hydrogenation of α-iminoesters was realized for the first time at 1 atm hydrogen pressure and room temperature. Pd(OAc)2, a less expensive Pd salt with low toxicity, was found to be the most suitable catalyst precursor rather than Pd(TFA)2 which is usually the catalyst of choice for homogeneous asymmetric hydrogenation. The chiral α-arylglycine fragments are widely found in many chiral products and bioactive molecules.

Palladium-Catalyzed Enantioselective Three-Component Synthesis of α-Arylglycines

A general Pd-catalyzed, enantioselective three-component synthesis of α-arylglycines starting from sulfonamides, glyoxylic acid derivatives, and boronic acids was developed. This operationally straightforward procedure enables the preparation of a wide variety of α-arylglycines in high yields and excellent levels of enantioselectivity from a simple set of readily available starting materials. Incorporation of Pbf-amides gives a racemization-free access to N-unprotected α-arylglycines.

One-step synthesis of racemic α-amino acids from aldehydes, amine components, and gaseous CO2 by the aid of a bismetal reagent

α-Amino acids are essential resources for human life and are highly useful as building blocks for organic synthesis. The core framework of an α-amino acid can be divided into three basic components: an aldehyde, an amine, and carbon dioxide (CO2). We report herein that a one-step synthesis of α-amino acids has been successfully achieved from these three basic and inexpensive chemicals with a single operation, in which the mixture of an aldehyde, a sulfonamide, and gaseous CO2 was heated at 100 °C in the presence of Bu3Sn-SnBu3 and CsF. In this one-pot sequential protocol, two important intermediates (imine and α-amino stannane) are involved and the stannyl anion generated in situ plays a crucial role, particularly for the efficient stannylation of the imine in the presence of proton sources and for promoting retrostannylation of the undesired α-alkoxy stannane owing to its high stability and tolerance of the presence of proton sources. This methodology enabled the synthesis of a wide range of racemic arylglycine derivatives in high yields. Go retro! α-Amino acids are essential resources for human life and are highly useful as building blocks for organic synthesis. The core framework of an α-amino acid is retrosynthesized to an aldehyde, an amine, and carbon dioxide. A one-step synthesis of α-amin Copyright

Enantioselective synthesis of diverse sulfinamides and sulfinylferrocenes from phenylglycine-derived chiral sulfinyl transfer agent

A new chiral sulfinyl transfer auxiliary derived from readily available phenylglycine was developed. This auxiliary is utilized to synthesize a diverse array of alkyl- and arylsulfinamides and sulfinylferrocenes in high yields and excellent ee's. The desired products are produced in a one-pot sequence from the oxathiazolidine 2-oxide by two sequential nucleophilic additions that proceed in a stereospecific manner.

Asymmetric synthesis of N-tosyl amino acids from N-sulfinyl α-amino-1,3-dithioketals

Hydrolysis of diastereomerically pure N-sulfinyl α-amino-1,3- dithianes with 1,3-dibromo-5,5-dimethylhydantoin gives N-tosyl α-amino aldehydes which when subjected to a Pinnick-type oxidation gave N-tosyl α-amino acids without epimerization.