116967-26-1

Basic information

• Product Name: TERT-BUTYL 3,5-DIOXOHEXANOATE
• Synonyms: TERT-BUTYL 3,5-DIOXOHEXANOATE;3,5-Dioxohexanoic acid tert-butyl ester;Hexanoic acid, 3,5-dioxo-, 1,1-diMethylethyl ester;3,5-Dioxo-heptenoic acid t-butyl ester
• CAS NO: 116967-26-1
• Molecular Formula: C10H16O4
• Molecular Weight: 200.232
• EINECS: 1592732-453-0
• Mol File: 116967-26-1.mol

Chemical Properties

• Boiling Point: 263.905 °C at 760 mmHg
• Flash Point: 109.764 °C
• Appearance: /
• Density: 1.046 g/cm³
• CAS DataBase Reference: TERT-BUTYL 3,5-DIOXOHEXANOATE(CAS DataBase Reference)
• NIST Chemistry Reference: TERT-BUTYL 3,5-DIOXOHEXANOATE(116967-26-1)
• EPA Substance Registry System: TERT-BUTYL 3,5-DIOXOHEXANOATE(116967-26-1)

Safety Data

• Hazardous Substances Data: 116967-26-1(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Synthetic Communications, 18, p. 735, 1988 DOI: 10.1080/00397918808077363

Upstream product

• 33400-61-2 t-Butyl 3-oxopentanoate 
• 1694-31-1 tert-butyl acetoacetate 
• 78191-00-1 N-Methoxy-N-methylacetamide 
• 125404-65-1 tert-butyl 5-hydroxy-4a-oxohexanoate 
• 84257-12-5 2,2-dimethyl-5-(1-hydroxy-3-oxobutylidene)-1,3-dioxane-4,6-dione 
• 75-65-0 tert-butyl alcohol 

Downstream Products

• 166803-31-2 (E)-7-[2-cyclopropyl-4-(4-fluoro-phenyl)-quinolin-3-yl]-3,5-dioxo-hept-6-enoic acid ethyl ester 
• 1344117-94-7 (E)-7-[4-(4-fluorophenyl)-6-isopropyl-2-[methyl(methylsulfonyl)amino]pyrimidin-5-yl]-(3R,5S)-3,5-hydroxy-6-heptenoic acid n-propylamine salt 
• 119067-60-6 (6R)-6-methyl-5,6-dihydro-2H-pyran-2-one 

Relevant articles and documents

Enzymatic reductions for the regio-and stereoselective synthesis of hydroxy-keto esters and dihydroxy esters

Ketoreductases were utilized for the stereoselective synthesis of δ-hydroxy-β-keto esters, β-hydroxy-δ-keto esters, and β,δ-dihydroxy esters. Seven out of eight possible stereoisomers were obtained from the enzymatic reduction of the corresponding β,δ-diketo ester in high enantio-and diastereomeric excess.

Addition of a polyhistidine tag alters the regioselectivity of carbonyl reductase S1 from: Candida magnoliae

Studying enzymatic reductions of substrates with more than a single keto group is challenging, as the carbonyl reduction can create a vast array of regio- and stereoisomers. If used as reference compounds, regio- and stereopure hydroxy ketides could facilitate the characterization of reductases with unclear regio- and stereoselectivity. We have combined nonenzymatic and enzymatic reduction and oxidation steps to obtain all four regio- and stereoisomers of tert-butyl hydroxyoxohexanoates in high optical purity (enantiomeric ratio (er) of 99:1 for the δ-hydroxy-β-keto isomers; er of >97:3 for the β-hydroxy-δ-keto isomers). Furthermore, we have prepared seven of the eight possible regioisomers and diastereomers of γ-methylated hydroxyoxohexanoates. These 11 compounds allowed unraveling the complex stereoselectivity of β,δ-diketo ester reductions catalyzed by carbonyl reductase S1 from Candida magnoliae (CMCR-S1). Our analysis shows that the regio- and stereoselectivity of CMCR-S1-catalyzed reductions is highly sensitive toward modifications at the C-terminus of CMCR-S1: in addition to the expected δ-hydroxy product, the variant with a C-terminal His-tag also led to formation of β-hydroxy by-products with high optical purity.

ROSUVASTATIN CALCIUM AND PROCESS FOR PRODUCING INTERMEDIATE THEREOF

An object of the present invention is to provide a novel method capable of producing rosuvastatin calcium and intermediates therefor efficiently, inexpensively and with high purity. The present invention provides a method of efficiently producing rosuvastatin calcium and intermediates therefor having a high purity at an industrial scale, without using an extremely low temperature reaction or a special asymmetric catalyst.

Ru-catalyzed hydrogenation of 3,5-diketo amides: Simultaneous control of chemo- and enantioselectivity

By modulating the chelating priorities of the different directing groups in 3,5-diketo amides with the assistance from coordinating solvent, highly chemo- and enantioselective hydrogenation of the C3-carbonyls was achieved in the presence of [RuCl(benzene)(S)-SunPhos]Cl in THF.

A total synthesis of xestodecalactone A and proof of its absolute stereochemistry: Interesting observations on dienophilic control with 1,3-disubstituted nonequivalent allenes

A concise total synthesis of xestodecalactone A, utilizing a Diels-Alder strategy is described. The focal Diels-Alder reaction relied on an "ynoate" dienophile to rapidly assemble the required resorcylinic acid scaffold. During this study, Diels-Alder cycloaddition reactions involving 1,3-disubstituted nonequivalent allene dienophiles were studied, and some surprising results were encountered.

A SIMPLE METHOD TO PREPARE ALKYL 3,5-DIOXOHEXANOATES

A simple and efficient method to prepare alkyl 3,5-dioxohexanoates by alcoholysis of isopropylidene (1-hydroxy-3-oxo-butylidene)malonate is described.