173065-16-2

Usage

Uses

Used in Organic Synthesis:
(S)-2,2-Dimethyl-3-(N-Boc)-4-ethynyl-oxazolidine is used as a building block in organic synthesis for the preparation of complex organic molecules. Its unique structural elements and reactivity allow for the creation of a variety of chemical entities, contributing to the advancement of chemical libraries and the development of novel compounds.
Used in Drug Discovery:
In the pharmaceutical industry, (S)-2,2-Dimethyl-3-(N-Boc)-4-ethynyl-oxazolidine is utilized as a pharmacophore in the design of new biologically active compounds. Its potential to be incorporated into drug molecules can lead to the discovery of new therapeutic agents with improved efficacy and selectivity.
Used in the Synthesis of Enantiopure Molecules:
The presence of a chiral center in (S)-2,2-Dimethyl-3-(N-Boc)-4-ethynyl-oxazolidine makes it a valuable intermediate for the synthesis of enantiopure molecules. This is particularly important in the pharmaceutical sector, where the stereochemistry of a drug can significantly impact its pharmacological properties and safety profile. The ability to produce enantiomerically pure compounds from this intermediate can facilitate the development of more effective and safer medications.

Upstream product

• 130418-98-3 (S)-tert-butyl 4-(2,2-dibromovinyl)-2,2-dimethyloxazolidine-3-carboxylate 
• 95715-87-0 (R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine 
• 90965-06-3 dimethyl 1-(1-diazo-2-oxopropyl)phosphonate 
• 1822572-30-4 4-(methoxymethylcarbamoyl)-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester 
• 4202-14-6 dimethyl (2-oxopropyl)phosphonate 
• 108149-60-6 methyl [(4R)-3-(tert-butoxycarbonyl)-2,2-dimethyl-1,3-oxazolidin-4-yl]carboxylate 

Downstream Products

• 1261060-24-5 (S)-tert-butyl 4-((2-formamido-4-methoxyphenyl)ethynyl)-2,2-dimethyloxazolidine-3-carboxylate 
• 1261060-16-5 (S)-tert-butyl 4-((2-formamidophenyl)ethynyl)-2,2-dimethyloxazolidine-3-carboxylate 
• 1261060-26-7 (S,Z)-tert-butyl 4-(2-isocyano-4-methoxystyryl)-2,2-dimethyloxazolidine-3-carboxylate 
• 1261060-25-6 (S,Z)-tert-butyl 4-(2-formamido-4-methoxystyryl)-2,2-dimethyloxazolidine-3-carboxylate 
• 1261060-18-7 (S,Z)-tert-butyl 4-(2-isocyanostyryl)-2,2-dimethyloxazolidine-3-carboxylate 
• 1261060-17-6 (S,Z)-tert-butyl 4-(2-formamidostyryl)-2,2-dimethyloxazolidine-3-carboxylate 
• 1293362-73-8 C₂₀H₂₆N₄O₃ 
• 1205640-67-0 (S)-4-[3-(4-chloro-phenyl)-3-hydroxy-prop-1-ynyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester 
• 275388-05-1 (S)-tert-butyl (1-hydroxybut-3-yn-2-yl)carbamate 

Relevant academic research and scientific papers

Synthesis of a Novel Rhizobitoxine-Like Triazole-Containing Amino Acid

The synthesis of the four stereoisomers of a new 1,2,3-triazole analogue of rhizobitoxine from serine is described. The key step is a Huisgen 1,3-dipolar cycloaddition on an ethynylglycine synthon.

Total synthesis of the COPD biomarker desmosine via stepwise Sonogashira cross-coupling reactions

Desmosine, a COPD biomarker and elastin crosslinker, is a tetrasubstituted pyridinium amino acid. In this paper, the total synthesis of desmosine is described utilizing stepwise and regioselective palladium-catalyzed Sonogashira cross-coupling reactions o

Total synthesis of COPD biomarker desmosine that crosslinks elastin

Desmosine, a crosslinking amino acid of elastin, is an attractive biomarker for diagnosis of chronic obstructive pulmonary disease (COPD). In this study, the first total synthesis of (+)-desmosine was achieved in 11% overall yield in 13 steps utilizing st

Total synthesis of tryprostatins A and B

Three distinct synthetic routes to the 2-prenyl tryptophan core skeleton of tryprostatins and their total syntheses are described. The strategies include a traditional gramine-mediated coupling reaction, Fuerstner indole synthesis, and our radical-mediated indole synthesis from o-alkenylphenyl isocyanide. The establishment of reliable conditions for the radical-mediated construction of indoles via a low-temperature radical initiator V-70 (2,2′-azobis(4- methoxy-2,4-dimethylvaleronitrile)) led to the highly efficient syntheses of tryprostatins A and B.

Total synthesis of tryprostatins a and b

A reasonable approach to the radical: The establishment of reliable conditions for the radical-mediated construction of indoles enabled the highly efficient synthesis of tryprostatins A and B. Use of the radical initiator 2,2′-azobis(4-methoxy-2,4-dimethylvaleronitrile) has allowed to carry out the radical cyclization at just 30°C, thereby suppressing the formation of by-products. Copyright

1,2-diastereoselective C-C bond-forming reactions for the synthesis of chiral β-branched α-amino acids

SN2′ sequences have been employed for the synthesis of β-branched α-amino acids using 1,2-diastereocontrol for forming C-C bonds. An oxazolidine fragment derived from Garner's aldehyde provides the handle for facial discrimination and acts as a

A reasonably stereospecific multistep conversion of Boc-protected α-amino acids to Phth-protected β3-amino acids

A method for the synthesis of β3-amino acids starting from α-amino acids is described. This conversion can be effected by an eight-step procedure which involves the transformation of the carboxylic group into an alkyne followed by a selenium-mediated conversion of the carbon-carbon triple bond to a Se-phenyl selenocarboxylate intermediate. The reactive Se-phenyl selenocarboxylate intermediates can be trapped with water, alcohols or the amine of an amino acid derivative to give β3-amino acids, β3-amino esters or mixed peptides, respectively. The whole transformations of the carboxylic group into an alkyne and of the alkyne group into β3-amino acids may not require purification of the intermediate products but a work-up and isolation procedure of crude materials.

Total synthesis of (+)-asperazine

The first total synthesis of the structurally novel cyclotryptophan alkaloid asperazine is reported. The central step in the synthetic sequence is a diastereoselective intramolecular Heck reaction in which the substituent controlling stereoselection is ex

A convenient scalable one-pot conversion of esters and Weinreb amides to terminal alkynes

Esters and amides undergo reduction to the corresponding aldehydes using DIBAL-H followed by same pot conversion to terminal alkynes utilizing the Bestmann-Ohira reagent in good to excellent yields. Additionally chiral nonracemic substrates undergo this transformation with complete preservation of stereochemical integrity.

Practical one-step synthesis of ethynylglycine synthon from Garner's aldehyde

A simple, efficient and practical synthesis of (R)-2,2-dimethyl-3-(tert-butoxycarbonyl)-4-ethynyloxazolidine (ethynylglycine synthon) is described. The method involves in situ formation of dimethyl 1-diazo-2-oxopropyl phosphonate from dimethyl 2-oxopropyl phosphonate and 4-acetamidobenzene sulfonyl azide and one-pot reaction on Garner's aldehyde. The reaction has been extended to other aminoaldehydes.