186521-82-4

Basic information

• Product Name: 1,3-Dioxolane, 4-ethynyl-2,2-dimethyl-, (R)- (9CI)
• Synonyms: 1,3-Dioxolane, 4-ethynyl-2,2-dimethyl-, (R)- (9CI)
• CAS NO: 186521-82-4
• Molecular Formula: C₇H₁₀O₂
• Molecular Weight: 126.1531
• Mol File: 186521-82-4.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1,3-Dioxolane, 4-ethynyl-2,2-dimethyl-, (R)- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-Dioxolane, 4-ethynyl-2,2-dimethyl-, (R)- (9CI)(186521-82-4)
• EPA Substance Registry System: 1,3-Dioxolane, 4-ethynyl-2,2-dimethyl-, (R)- (9CI)(186521-82-4)

Safety Data

• Hazardous Substances Data: 186521-82-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
1,3-Dioxolane, 4-ethynyl-2,2-dimethyl-, (R)(9CI) is used as a synthetic intermediate and reagent for the formal synthesis of Ezetimibe (E975000). It is involved in a Cu(I)-mediated Kinugasa cycloaddition/rearrangement cascade reaction, which is a key step in the production of this cholesterol-lowering drug. This application is significant as it contributes to the development and manufacturing of an essential medication for managing high cholesterol levels and related health conditions.

Upstream product

• 60456-21-5 methyl (4S)-2,2-dimethyl-1,3-dioxolane-4-carboxylate 
• 90965-06-3 dimethyl 1-(1-diazo-2-oxopropyl)phosphonate 
• 22323-80-4 (4S)-2,2-dimethyl-[1,3]dioxolane-4-carbaldehyde 
• 56017-84-6 4-(2,2-Dibromoethenyl)-2,2-dimethyl-1,3-dioxolane 
• 116-11-0 2-Methoxypropene 
• 118620-89-6 (R)-1-butyne-3,4-diol 

Downstream Products

• 1415345-64-0 (5S,6R,7S,4'R)-5-benzyloxy-7-(2′,2′-dimethyl-1′,3′-dioxolan-4′-yl)-1-azabicyclo[4.2.0]octan-8-one 
• 1415345-81-1 (5S,6R,7R,4'R)-5-benzyloxy-7-(2′,2′-dimethyl-1′,3′-dioxolan-4′-yl)-1-azabicyclo[4.2.0]octan-8-one 
• 1415704-17-4 C₂₀H₂₀FNO₃ 
• 1415704-32-3 C₂₀H₂₀FNO₃ 
• 1415704-33-4 C₂₀H₂₀FNO₃ 
• 1415704-34-5 C₂₀H₂₀FNO₃ 
• 1415704-18-5 C₂₇H₂₆FNO₆S 
• 1415704-35-6 C₂₇H₂₆FNO₆S 
• 1415704-36-7 C₂₇H₂₆FNO₆S 
• 1415704-37-8 C₂₇H₂₆FNO₆S 
• 1415704-19-6 C₂₁H₂₂FNO₆S 
• 1415704-41-4 C₂₁H₂₂FNO₆S 
• 1415704-42-5 C₂₁H₂₂FNO₆S 
• 1415704-43-6 C₂₁H₂₂FNO₆S 

Relevant articles and documents

Diastereoselective synthesis of β-lactams via Kinugasa reaction of acyclic chiral nitrones

An approach to β-lactams via a Kinugasa reaction between chiral copper acetylides and chiral acyclic nitrones bearing either 1,3-dioxane or 1,3-dioxolane moieties is reported. The stereochemical preferences observed in these reactions are discussed. The reaction provides access to a variety of interesting β-lactam structures. Electronic circular dichroism in combination with NMR spectroscopy was shown to be a useful and effective method for the reliable determination of the absolute configuration of all components of a complex mixtures of azetidinones. The effectiveness of the chiral analysis of complex mixtures was demonstrated for HPLC coupled on-line with electronic circular dichroism detection as well.

A PROCESS FOR THE PREPARATION OF AN ALDEHYDE BETA-LACTAM COMPOUND

The invention relates to a process for the preparation of an aldehyde beta-lactam compound of formula (I), wherein P1 is H or a protecting group, useful in the preparation of ezetimibe, from a nitrone compound of formula (II). The nitrone compound Il is prepared by reacting 4-fluorophenylhydroxyloamine with OH- protected 4-hydroxybenzaldehyde. The nitrone compound of formula (II) is reacted with an acetylene compound of formula (III) to form a compound of formula (IV), and the compound of formula (IV), after optional deprotection, is oxidized to obtain an aldehyde of formula (V), which undergoes isomerisation to the compound of formula (I). The subject of the invention are also novel compounds of formulas (II) and (IV).

Enantiomerically pure cyclopropylboronic esters: Auxiliary- versus substrate-control

Stable, enantiomerically pure cyclopropylboronic esters are synthesized from alkynes by a hydroboration-cyclopropanation sequence. The direct hydroboration - utilizing 1,3,2-dioxaborolane 4 - is most convenient, however, with more functionalized side-chains it failed to give the desired intermediates. Using the more reactive dicyclohexylborane, followed by oxidation and transesterification, is a good alternative one-pot conversion. Cyclopropanations were performed either following a Simmons-Smith protocol or with diazomethane-palladium(II) acetate. The influence on the diastereoselectivity of the auxiliary 1 is compared with the influence of an additional stereogenic center in the side-chain. The Royal Society of Chemistry 2000.

Lipase-mediated preparation of optically pure four-carbon di- and triols from a meso-precursor

An expedient route to optically pure four-carbon di- and triols, prepared from a meso-symmetric four-carbon precursor by employing lipase-mediated kinetic resolution as a key step.