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SN2 Reaction: Stereochemistry02:23

SN2 Reaction: Stereochemistry

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In an SN2 reaction, the nucleophilic attack on the substrate and departure of the leaving group occurs simultaneously through a transition state. As the nucleophile approaches the substrate from the back-side, the configuration of the substrate carbon changes from tetrahedral to trigonal bipyramidal and then back to tetrahedral, leading to an inversion in the configuration of the product.
If the substrate is an achiral molecule at the α-carbon, the inversion of configuration is not...
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SN1 Reaction: Stereochemistry02:15

SN1 Reaction: Stereochemistry

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This lesson provides an in-depth discussion of the stereochemical outcomes in an SN1 reaction.
In the first step of an SN1 reaction, the bond between the electrophilic carbon and the leaving group ionizes to generate the carbocation intermediate. The second step of the mechanism is the nucleophilic attack.
In the formed carbocation, the positively charged carbon is sp2 hybridized with a trigonal planar geometry. As all the three substituents lie on the same plane, a plane of symmetry for the...
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Regioselectivity of Electrophilic Additions to Alkenes: Markovnikov's Rule02:17

Regioselectivity of Electrophilic Additions to Alkenes: Markovnikov's Rule

16.3K
If a set of reactants can yield multiple constitutional isomers, but one of the isomers is obtained as the major product, the reaction is said to be regioselective. In such reactions, bond formation or breaking is favored at one reaction site over others.
The hydrohalogenation of an unsymmetrical alkene can yield two haloalkane products, depending on which vinylic carbon takes up the halogen. However, one product usually predominates, where hydrogen adds to the vinylic carbon bearing the...
16.3K
Regioselectivity and Stereochemistry of Hydroboration02:36

Regioselectivity and Stereochemistry of Hydroboration

9.4K
A significant aspect of hydroboration–oxidation is the regio- and stereochemical outcome of the reaction.
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn stereochemistry.
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α-Alkylation of Ketones via Enolate Ions01:10

α-Alkylation of Ketones via Enolate Ions

3.8K
Ketones with α protons are deprotonated by strong bases like lithium diisopropylamide (LDA) to form enolate ions. The anion is stabilized by resonance, and its hybrid structure exhibits negative charges on the carbonyl oxygen and the α carbon. This ambident nucleophile can attack an electrophile via two possible sites: the carbonyl oxygen, known as O-attack, or the α carbon, known as C-attack. The nucleophilic attack via the carbanionic site is preferred. This is due to the...
3.8K
Nucleophilic Aromatic Substitution: Addition–Elimination (SNAr)01:30

Nucleophilic Aromatic Substitution: Addition–Elimination (SNAr)

4.6K
Nucleophilic substitution in aromatic compounds is feasible in substrates bearing strong electron-withdrawing substituents positioned ortho or para to the leaving group. The reaction proceeds via two steps: the addition of the nucleophile and the elimination of the leaving group.
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Stereoselective Anomeric Phosphorylation under Modified Mitsunobu Reaction Conditions.

Alessandro Monti1, Biswajit Sarkar1, Alla Zamyatina1

  • 1Department of Natural Sciences and Sustainable Resources, Institute of Organic Chemistry, BOKU University, Muthgasse 18, Vienna A-1190, Austria.

The Journal of Organic Chemistry
|September 24, 2025
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Summary

Synthesizing glycosyl phosphates with specific configurations is challenging. A modified Mitsunobu reaction provides stereoselective synthesis of difficult β-heptosyl phosphates, crucial for immune signaling molecules.

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Area of Science:

  • Carbohydrate Chemistry
  • Organic Synthesis
  • Biochemistry

Background:

  • Glycosyl phosphates are essential biomolecule components and biosynthetic intermediates.
  • Limited availability necessitates stereoselective synthesis methods for defined anomeric configurations.
  • Synthesis of specific β-heptosyl phosphates is challenging, particularly for ADP-heptose precursors involved in innate immune signaling.

Purpose of the Study:

  • To develop a stereoselective method for synthesizing challenging glycosyl phosphates, especially those with the opposite anomeric configuration to the starting lactol.
  • To investigate reaction mechanisms for controlling anomeric configuration during glycosyl phosphate synthesis.
  • To enable efficient production of precursors for pathogen-associated molecular patterns like ADP-heptose.

Main Methods:

  • Modification of the Mitsunobu reaction for stereospecific anomeric phosphorylation.
  • NMR spectroscopy for mechanistic studies to differentiate reaction pathways (inversion vs. retention).
  • Identification of (diglycosyloxy)phosphoranes as key reactive intermediates.

Main Results:

  • Successful stereoselective synthesis of challenging β-heptosyl phosphates.
  • Elucidation of reaction pathways involving either inversion or retention of anomeric configuration.
  • Development of specialized protocols using identified reactive species for controlled synthesis.

Conclusions:

  • A modified Mitsunobu reaction enables efficient and stereoselective synthesis of glycosyl phosphates.
  • Mechanistic insights allow control over anomeric configuration (inversion via SN2 or retention).
  • This method facilitates the synthesis of crucial precursors for studying innate immune responses.