133464-36-5

Usage

Uses

Used in Pharmaceutical Industry:
(S)-hydroxymethyl-2,2-dimethyloxazolidine-3-carboxylic acid benzyl ester is used as a chiral building block for the synthesis of various pharmaceuticals. Its unique structure allows for the creation of a wide range of compounds with potential therapeutic applications.
Used in Chemical Industry:
In the chemical industry, (S)-hydroxymethyl-2,2-dimethyloxazolidine-3-carboxylic acid benzyl ester is used as a chiral auxiliary in asymmetric synthesis. This application is crucial for the production of enantiomerically pure compounds, which are essential in various chemical processes and products.
Used in Agrochemicals:
(S)-hydroxymethyl-2,2-dimethyloxazolidine-3-carboxylic acid benzyl ester is also utilized as a reagent in the preparation of intermediate compounds for agrochemicals. Its role in this industry highlights its versatility and importance in the development of new and improved products for agricultural applications.
Used in Medicinal Chemistry and Drug Development:
Due to its unique chemical properties and structural characteristics, (S)-hydroxymethyl-2,2-dimethyloxazolidine-3-carboxylic acid benzyl ester has potential applications in medicinal chemistry and drug development. Researchers can leverage its chiral nature to design and synthesize novel compounds with potential therapeutic benefits.

Upstream product

• 93204-36-5 (R)-methyl 2-(((benzyloxy)carbonyl)amino)-3-hydroxypropanoate 
• 501-53-1 benzyl chloroformate 
• 133464-37-6 (4R)-4-formyl-2,2-dimethyloxazolidine-3-carboxylic acid benzyl ester 
• 133464-35-4 3-benzyl 4-methyl (4R)-2,2-dimethyloxazolidine-3,4-dicarboxylate 

Downstream Products

• 176311-99-2 benzyl (4R)-2,2-dimethyl-4-(p-toluenesulfonyloxymethyl)oxazolidine-3-carboxylate 
• 1311159-08-6 (S)-benzyl-2,2-dimethyl-4-(tert-amylamino)methyl-1,3-oxazolidine-3-carboxylate 
• 1150635-61-2 N-benzyloxycarbonyl-3-hydroxy-4-methoxy-5-methyl-L-phenylalaninol 
• 271260-80-1 (S)-3-(benzyloxycarbonyl)-2,2-dimethyl-4-vinyloxazolidine 
• 914498-28-5 benzyl (4R)-2,2-dimethyl-4-({[(4-nitrophenyl)sulfonyl]oxy}methyl)-1,3-oxazolidine-3-carboxylate 
• 1325208-63-6 C₃₃H₃₅BrN₂O₅ 
• 1325208-62-5 C₃₃H₃₆N₂O₆ 
• 1187326-80-2 (S)-benzyl 2,2-dimethyl-4-(m-tolyloxymethyl)oxazolidine-3-carboxylate 
• 1187326-82-4 (S)-benzyl-2,2-dimethyl-4-[(naphthalen-1-yloxy)methyl]oxazolidine-3-carboxylate 
• 510714-09-7 N-Cbz-(2S)-4,4-difluoroglutamic acid α-tert-butyl ester γ-glutamic acid α-tert-butyl γ-2-(trimethylsilyl)ethyl ester 

Relevant academic research and scientific papers

Tetrahydroisoquinoline intermediate of compound preparation method

The invention provides a tetrahydroisoquinoline compound with the following structural general formula I. The invention also provides application of the above tetrahydroisoquinoline compound as an intermediate for the preparation of tetrahydroisoquinoline alkaloid natural medicaments. The invention further provides a method for preparing the tetrahydroisoquinoline compound. The method uses a halogenated aromatic compound as a starting material, and conducts nucleophilic substitution, addition, hydroxy elimination and protecting group elimination reaction, thereby obtaining the tetrahydroisoquinoline compound with chiral amine.

Design, synthesis and structure-activity relationship studies of a novel focused library of 2,3,4-substituted oxazolidines with antiproliferative activity against cancer cell lines

In the present work we describe the synthesis and antiproliferative evaluation of a focused library of 30 novel oxazolidines designed by modification of N-substituent, by ring variation, by alkyl variation or by extension of the structure. It was noted that carbamate and N,O-aminal groups were essential for activity. In general, replacement of the phenyl ring with pyridinyl was not tolerated. However, the introduction of a second phenyl ring with an appropriate spacer at the 3- or 4-position of the first phenyl ring generally enhanced the cytotoxic profile. Among all the prepared compounds, 24 was the most potent compound found in this class, being active on four of five cancer cell lines and it was 5-fold and 10-fold more potent than the lead compounds against HL60 and JURKAT cells, respectively. In addition, it showed relevant activity against MCF-7 and HCT-116 cells, which were resistant to lead. Moreover, 24 showed little antiproliferative activity against VERO, indicating low toxicity to normal cells. Thus, this compound has the potential to be developed as an anticancer agent.

Development of a scalable chiral synthesis of MK-3281, an inhibitor of the hepatitis C virus NS5B polymerase

The development of a scalable chiral synthesis for the HCV NS5B inhibitor MK-3281 is being reported. Several alternative routes were explored and are being described. Georg Thieme Verlag Stuttgart ? New York.

Rearrangement of N-alkyl 1,2-amino alcohols. Synthesis of (S)-toliprolol and (S)-propanolol

N-alkyl 1,2-amino alcohols were rearranged stereospecifically by using TFAA/Et3N. This rearrangement has been used to synthesize N-isopropyl-3-(aryloxy)-2-hydroxypropylamines, β-adrenergic blocking agents such as (S)-toliprolol and (S)-propanolol.

The synthesis of (2S)-4,4-difluoroglutamyl γ-peptides based on Garner's aldehyde and fluoro-reformatsky chemistry

The development of optically active fluorinated synthetic building blocks of general utility is a current goal of organo-fluorine chemists. The serine-derived Garner aldehyde was converted to a general 4,4-difluoroamino acid building block via fluoro-Reformatsky reaction with ethyl bromodifluoroacetate. The utility of this building block was demonstrated by the synthesis of derivatives of (2S)-4,4-difluoroglutamine, (2S)-4,4-difluoroglutamic acid, and its incorporation into a fluorophore-containing isopeptide 2 designed as a mechanistic probe of γ-glutamyl hydrolase. Compound 2 proved to be a substrate for γ-glutamyl hydrolase and was hydrolyzed at a rate significantly slower than the corresponding non-fluorinated analog.

Enantiospecific synthesis of (R)- and (S)-2,3-diaminopropanol from L- and D-serine

Both chiral forms of 2,3-diaminopropanol (6) have been prepared in a convenient 5-step synthesis based on the readily available N-benzyloxycarbonyl derivatives of the methyl esters of L- and D-serine.