201404-86-6

Usage

Uses

Used in Organic Synthesis:
(R)-TERT-BUTYL 4-(2-HYDROXYETHYL)-2,2-DIMETHYLOXAZOLIDINE-3-CARBOXYLATE is used as a chiral auxiliary for enhancing the selectivity of asymmetric synthesis reactions, enabling the production of enantiomerically pure compounds.
Used in Pharmaceutical Industry:
(R)-TERT-BUTYL 4-(2-HYDROXYETHYL)-2,2-DIMETHYLOXAZOLIDINE-3-CARBOXYLATE is used as a catalyst or ligand in various chemical reactions, contributing to the development of pharmaceutical compounds with improved efficacy and selectivity.
Used in Agrochemical Industry:
(R)-TERT-BUTYL 4-(2-HYDROXYETHYL)-2,2-DIMETHYLOXAZOLIDINE-3-CARBOXYLATE is employed in the synthesis of agrochemicals, particularly in the production of chiral pesticides and herbicides, to enhance their effectiveness and reduce environmental impact.

Upstream product

• 115378-31-9 tert-butyl (4R)-2,2-dimethyl-4-vinyloxazolidine-3-carboxylate 
• 428440-11-3 D-Boc-L-Asp(OEt)OEt 
• 77-76-9 2,2-dimethoxy-propane 
• 397246-14-9 (1-(hydroxymethyl)-3-hydroxypropyl)carbamic acid tert-butyl ester 
• 102308-32-7 (4S)-4-formyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester 
• 18107-18-1 diazomethyl-trimethyl-silane 

Downstream Products

• 153053-19-1 (4R)-2,2-dimethyl-4-(2-oxoethyl)-oxazolidine-3-carboxylic acid tert-butyl ester 

Relevant academic research and scientific papers

6,7-DIHYDRO-5H-PYRIDO[2,3-C]PYRIDAZINE DERIVATIVES AND RELATED COMPOUNDS AS BCL-XL PROTEIN INHIBITORS AND PRO-APOPTOTIC AGENTS FOR TREATING CANCER

The present invention discloses 6,7-dihydro-5H-pyrido[2,3- c]pyridazine, 1,2,3,4-tetrahydroquinoline, 1H-indole, 3,4- dihydro-2H-1,4-benzoxazine, 1H-pyrrolo[2,3-b]pyridin-1-yl, 7H- pyrrolo[2,3-c]pyridazine, 5H,6H,7H,8H,9H-pyridazino[3,4-b]azepine derivatives and related compounds of formula (I) as Bcl-xL protein inhibitors for use as pro-apoptotic agents for treating cancer, autoimmune diseases or immune system diseases. Formula (I). The description discloses the preparation of exemplary compounds (e.g. pages 113 to 354 examples 1 to 221) as well as pharmacological studies with relevant data (e.g. pages 355 to 367; examples A to E; tables 1 to 5). Exemplary compounds are e.g. 2-{6-[(1,3-benzothiazol-2-yl) amino]-1,2,3,4-tetrahydroquinolin-1-yl}-1,3-thiazole-4-carboxylic acid (example 1) or e.g. 3-{1-[(adamantan-1-yl)methyl]-5- methyl-1H-pyrazol-4-yl}-6-{3-[(1,3-benzothiazol-2-yl)amino]-4- methyl-5H,6H,7H,8H-pyrido[2,3-c]pyridazin-8-yl]pyridine-2-carboxylic acid (example 24).

A west he row sandbank intermediate preparation method

The invention discloses a preparation method for a sitagliptin intermediate and belongs to the field of drug synthesis. The preparation method comprises the following steps: (1) carrying out a ring-opening reaction: carrying out Grignard reaction on 2,4,5-trifluorobromobenzene and a Grignard reagent RMgX in a medium of tetrahydrofuran and methyl tertiary-butyl ether at (-20) DEG C to 50 DEG C by taking cuprous chloride as a catalyst, wherein R2 is isopropyl and X is halogen, and then carrying out the ring-opening reaction on the generated compound and a compound shown in a formula 3 to obtain a compound shown in a formula 4; and (2) carrying out an oxidizing reaction: carrying out the oxidizing reaction on the compound shown in the formula 4 and potassium permanganate in an acetone medium, quenching and neutralizing the product by using reducing agents sodium sulfite and sodium hydrogen sulfite, and extracting the product by methyl tertiary butyl ether to obtain the sitagliptin intermediate. The method is low in cost, high in yield, mature in process and suitable for industrial production.

THIADIAZOLE MODULATORS OF S1P AND METHODS OF MAKING AND USING

The invention is directed to compounds of the formula: wherein each of the variables are defined herein, as well as methods of making and using the compounds as agonists of S1P1 and/or S1P5 for instance treating an autoimmune disease.

A stereoselective total synthesis of (-)-andrachcinidine via an olefin cross-metathesis protocol

A stereoselective total synthesis of 1-(2S,6R)-6-[(2S)-2-hydroxypentyl]-hexahydro-2-pyridinylacetone, (-)-andrachcinidine is reported. The strategy utilizes olefin cross-metathesis and intramolecular SN2 cyclization as the key steps.

A new stereocontrolled approach to a key intermediate in the synthesis of (25,3R)-capreomycidine

A new stereocontrolled approach to the synthesis of advanced intermediate in the synthesis of nonproteinogenic amino acid (2S,3R)-capreomycidine via the novel domino reaction has been developed.

Rhodium-catalyzed cascade reactions: A methylenation-hydroboration homologative process

A very efficient rhodium-catalyzed cascade process allowing the transformation of aldehydes and ketones into their corresponding one or two-carbon homologated alcohol products through a methylenation-hydroboration sequence is reported. Wilkinson's complex is used to catalyze both reactions in a one-pot procedure that does not require the isolation of the alkene intermediate.

Enantiomerically pure α-amino acid synthesis via hydroboration - Suzuki cross-coupling

The Garner aldehyde-derived methylene alkene 5 and the corresponding benzyloxycarbonyl compound 25 undergo hydroboration with 9-BBN-H followed by palladium-catalyzed Suzuki coupling reactions with aryl and vinyl halides. After one-pot hydrolysis -oxidation, a range of known and novel nonproteinogenic amino acids were isolated as their N-protected derivatives. These novel organoborane homoalanine anion equivalents are generated and transformed under mild conditions and with wide functional group tolerance: electron-rich and -poor aromatic iodides and bromides (and a vinyl bromide) all undergo efficient Suzuki coupling. The extension of this methodology to prepare meso-DAP, R,R-DAP, and R,R-DAS is also described.

The synthesis of novel amino acids via hydroboration-suzuki cross coupling

The Gamer aldehyde-derived methylene alkene has been hydroborated using 9-BBN and the resulting organoborane employed in palladium-catalysed Suzuki coupling reactions to produce, after hydrolysis-oxidation, a range of novel amino acids as their N-BOC protected derivatives.

Synthesis of sphingosine analogues: Stereoselective synthesis of 3- deoxysphingosine and cis-isomers

Both enantiomers of 3-deoxysphingosine as well as their cis-isomers were synthesized stereoselectively from L- and D-serine.