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Related Concept Videos

SN2 Reaction: Stereochemistry02:23

SN2 Reaction: Stereochemistry

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 observed.
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry01:29

Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry

Diels–Alder reactions between cyclic dienes locked in an s-cis configuration and dienophiles yield bridged bicyclic products.
Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation02:47

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

Introduction
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.
Preparation of Diols and Pinacol Rearrangement01:57

Preparation of Diols and Pinacol Rearrangement

Compounds bearing two hydroxyl groups are known as diols. When the hydroxyl groups are located on adjacent carbon atoms, the diols are called vicinal diols or glycols. Under acidic conditions, vicinal diols undergo a specific reaction called pinacol rearrangement.
The reaction begins with transferring a proton from the acid catalyst to one of the hydroxyl groups, producing an oxonium ion.
Hydroboration-Oxidation of Alkenes03:08

Hydroboration-Oxidation of Alkenes

In addition to the oxymercuration–demercuration method, which converts the alkenes to alcohols with Markovnikov orientation, a complementary hydroboration-oxidation method yields the anti-Markovnikov product. The hydroboration reaction, discovered in 1959 by H.C. Brown, involves the addition of a B–H bond of borane to an alkene giving an organoborane intermediate. The oxidation of this intermediate with basic hydrogen peroxide forms an alcohol.
Conjugate Addition to α,β-Unsaturated Carbonyl Compounds01:09

Conjugate Addition to α,β-Unsaturated Carbonyl Compounds

α,β-Unsaturated carbonyl compounds are molecules bearing a carbonyl and alkene functionality in conjugation with each other. The conjugation in the molecule leads to three resonance structures. The hybrid form exhibits two probable electrophilic sites: the carbonyl carbon and the β carbon.

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Regioselective O-Glycosylation of Nucleosides via the Temporary 2',3'-Diol Protection by a Boronic Ester for the Synthesis of Disaccharide Nucleosides
08:46

Regioselective O-Glycosylation of Nucleosides via the Temporary 2',3'-Diol Protection by a Boronic Ester for the Synthesis of Disaccharide Nucleosides

Published on: July 26, 2018

L-(+)-Bornesitol.

Denise C Endringer1, John M Pezzuto, Cristiane M Soares

  • 1Faculdade de Farmácia, Universidade Federal, de Minas Gerais, Av. Antônio, Carlos, 6627; CEP31270-901, Belo Horizonte, Brazil.

Acta Crystallographica. Section E, Structure Reports Online
|November 18, 2008
PubMed
Summary
This summary is machine-generated.

The crystal structure of a myo-inositol derivative (C7H14O6) was determined. Its structural parameters, including atom distances and bond lengths, closely resemble those of myo-inositol.

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Area of Science:

  • Biochemistry
  • Structural Biology
  • Organic Chemistry

Background:

  • Myo-inositol is a vital cyclic polyol involved in numerous cellular processes.
  • Understanding the structural variations of myo-inositol derivatives is crucial for elucidating their biological functions.
  • The specific derivative C7H14O6 is a naturally occurring compound with potential biological relevance.

Purpose of the Study:

  • To determine the precise three-dimensional structure of the natural myo-inositol derivative C7H14O6.
  • To compare the structural characteristics of C7H14O6 with the parent compound, myo-inositol.
  • To provide foundational structural data for future functional studies of this myo-inositol derivative.

Main Methods:

  • Single-crystal X-ray diffraction analysis was employed to determine the molecular structure.
  • Crystallographic data were collected and processed to obtain electron density maps.
  • The structure was refined to achieve convergence, yielding precise atomic coordinates.

Main Results:

  • The crystal structure of C7H14O6 was successfully elucidated.
  • Key structural parameters, including average atom distances, bond lengths, and dihedral angles, were accurately measured.
  • Comparisons revealed that these parameters are highly similar to those reported for myo-inositol.

Conclusions:

  • The determined structure of C7H14O6 is consistent with it being a natural myo-inositol derivative.
  • The structural similarity suggests conserved stereochemistry and bonding within the myo-inositol scaffold.
  • This structural data serves as a critical reference for understanding the chemical and potentially biological properties of C7H14O6.