104755-57-9

Upstream product

• 104755-56-8 (E)-3-(Triphenylsilyl)<2,3-(2)H2>prop-2-en-1-ol 
• 76-86-8 Triphenylsilyl chloride 
• 51105-91-0 3-(triphenylsilyl)propargyl alcohol 

Downstream Products

• 1612775-93-5 [4,5-²H₂]-(4S,5R)-2,2-dimethyl-5-(triphenylsilyl)-1,3-dioxolane-4-carbaldehyde 
• 104832-79-3 (2R,3S)-2-(triphenylsilyl)<2,3-(2)H2>oxirane 
• 104832-82-8 (2S,3R)-2-(triphenylsilyl)<2,3-(2)H2>oxirane 
• 59231-26-4 cis-α,β-Dideuterioepoxyaethyl-(triphenyl)-silan 
• 104755-58-0 (2R,3R)-3-(triphenylsilyl)<2,3-(2)H2>oxiranecarboxaldehyde 
• 104832-81-7 (2S,3S)-3-(triphenylsilyl)<2,3-(2)H2>oxiranecarboxaldehyde 

Relevant academic research and scientific papers

Imaging the absolute configuration of a chiral epoxide in the gas phase

In chemistry and biology, chirality, or handedness, refers to molecules that exist in two spatial configurations that are incongruent mirror images of one another. Almost all biologically active molecules are chiral, and the correct determination of their absolute configuration is essential for the understanding and the development of processes involving chiral molecules. Anomalous x-ray diffraction and vibrational optical activity measurements are broadly used to determine absolute configurations of solid or liquid samples. Determining absolute configurations of chiral molecules in the gas phase is still a formidable challenge. Here we demonstrate the determination of the absolute configuration of isotopically labeled (R,R)-2,3-dideuterooxirane by foil-induced Coulomb explosion imaging of individual molecules. Our technique provides unambiguous and direct access to the absolute configuration of small gas-phase species, including ions and molecular fragments.

Synthesis of Cryptochiral (R,R)-2,3-Dideuterooxirane as Stereochemical Reference Compound and Chemical Correlation with D-(+)-Glyceraldehyde

Chirality plays a pivotal role in chemistry and biology, e.g., structure-specific targeting in drug development or the lock-and-key theory of enzyme interactions. Determining absolute configurations of chiral molecules is essential to understanding such mechanisms and to developing chemical processes involving chiral compounds. In particular, this becomes obvious in the understanding of chemical reaction networks in the context of the origins of life. A stereochemical reference compound that can be correlated with sugars, amino acids, etc. is of great interest. Here, we present the synthesis of enantiopure (R,R)-2,3-dideuterooxirane, of which the absolute configuration has been unambiguously determined by foil-induced Coulomb explosion imaging, and the correlation with the configuration of D-(+)-glyceraldehyde.

Coulomb explosion imaged cryptochiral (R,R)-2,3-dideuterooxirane: Unambiguous access to the absolute configuration of (+)-glyceraldehyde

The absolute configuration of (R,R)-2,3-dideuterooxirane, which has been independently determined using Coulomb explosion imaging, has been unambiguously chemically correlated with the stereochemical key reference (+)-glyceraldehyde. This puts the absolute configuration of D(+)-glyceraldehyde on firm experimental grounds. 100% Absolute: The absolute configuration of (R,R)-2,3-dideuterooxirane, which has been independently determined by Coulomb explosion imaging (CEI), has been unambiguously chemically correlated with the stereochemical key reference (+)-glyceraldehyde. This puts the absolute configuration of D(+)-glyceraldehyde on firm experimental grounds (see scheme).

Synthesis of (2R,3R)- and (2S,3S)-Oxirane and Application of It to the Synthesis of Chirally Labeled Homoserine

(2R,3R)- and (2S,3S)-oxirane have been synthesized from 2-propynol, the key step being the asymmetric epoxidation of (E)-3-(triphenylsilyl)-2-propenol.To determine the enantiomeric purities of the oxiranes, they were reacted with phenyllithium,

Chirally-labelled Oxirane

(R,R)- and (S,S)-oxiranes have been synthesized from prop-2-yn-1-ol, the key step being asymmetric epoxidation of (E)-3-(triphenylsilyl)prop-2-en-1-ol.