108350-21-6

Basic information

• Product Name: TERT-BUTYL 3-OXOPROPIONATE
• Synonyms: TERT-BUTYL 3-OXOPROPIONATE;tert-Butyl forMylacetate;DJXQBXDUGONRMQ-UHFFFAOYSA-N
• CAS NO: 108350-21-6
• Molecular Formula: C₇H₁₂O₃
• Molecular Weight: 144.16838
• EINECS: -0
• Mol File: 108350-21-6.mol
• Article Data: 11

Chemical Properties

• Appearance: /
• CAS DataBase Reference: TERT-BUTYL 3-OXOPROPIONATE(CAS DataBase Reference)
• NIST Chemistry Reference: TERT-BUTYL 3-OXOPROPIONATE(108350-21-6)
• EPA Substance Registry System: TERT-BUTYL 3-OXOPROPIONATE(108350-21-6)

Safety Data

• Hazardous Substances Data: 108350-21-6(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Synthesis, p. 672, 1986 DOI: 10.1055/s-1986-31745

Upstream product

• 72793-38-5 2,2-dimethyl-4,6-dioxo-1,3-dioxane-5-carbaldehyde 
• 75-65-0 tert-butyl alcohol 
• 15568-87-3 5-(hydroxymethylene)-2,2-dimethyl-1,3-dioxan-4,6-dione 
• 1414926-72-9 (E)-di(tert-butyl) 3-hexenedioate 

Downstream Products

• 913845-59-7 (E/Z)-tert-butyl 3-(2-(3-(2,6-dichlorophenyl)isoxazol-5-yl)pyridin-4-ylamino)acrylate 
• 355806-00-7 rosuvastatin tert-butyl ester 
• 5751-20-2 2-Methylthiouracil 
• 93636-56-7 tert-butyl 3-hydroxy-5-phenyl-4-pentynoate 

Relevant articles and documents

An efficient procedure for the synthesis of formylacetic esters

An efficient synthesis of formylacetic esters via ozonolysis of trans-β-hydromuconic esters followed by a solid-supported triphenylphosphine reduction has been developed. In addition, an extension toward formylacetic amides and a one-pot preparation of more stable intermediates which can be used for further transformations are also described.

Scope and diastereoselectivity of the interrupted Feist-Benary reaction.

[reaction: see text] The base-promoted condensation of beta-dicarbonyl compounds with alpha-haloketones, the Feist-Benary reaction, conveniently produces highly substituted dihydrofurans. We show here that this reaction is quite general with respect to the nature of the beta-dicarbonyl compound, proceeding with beta-ketoesters, beta-oxopropionates, beta-diketones, and beta-dialdehydes. We also show that the diastereoselectivity of this reaction depends on the acidity of the nucleophile.

Orthogonally Protected Diaminoterephthalate Scaffolds: Installation of Two Functional Units at the Chromophore

The 2,5-diaminoterephthalate structural motif is a powerful chromophore with remarkable fluorescence properties. Containing two carboxylate and two amino functions, it defines a colored molecular scaffold which allows for orthogonal functionalization with different functional units. Therefore, different applications in life sciences and materials science could be addressed. In this study, the two amino functions were alkylated by reductive amination with side chains carrying amino (orthogonally protected as Boc or Alloc) and carboxylate functions (orthogonally protected as tBu or allyl ester). After sequential deprotections, functional units were introduced by amidation reactions. As three examples, the chromophore was coupled with retinoic acid and fullerene C60 in order to obtain a triad for studying photoinduced electron transfer processes. Furthermore, cyclooctyne and azide moieties were introduced as functional units, allowing for ligation by click reactions. These two clickable groups were applied in combination with maleimide units which are reactive toward thiol residues. The latter dyes define so-called turn on probes, since the fluorescence quantum yields increased by one order of magnitude upon reaction with the molecular target.