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Preparation and Reactions of Sulfides

Preparation and Reactions of Sulfides

Sulfides are the sulfur analog of ethers, just as thiols are the sulfur analog of alcohol. Like ethers, sulfides also consist of two hydrocarbon groups bonded to the central sulfur atom. Depending upon the type of groups present, sulfides can be symmetrical or asymmetrical. Symmetrical sulfides can be prepared via an SN2 reaction between 2 equivalents of an alkyl halide and one equivalent of sodium sulfide.

Preparation and Reactions of Thiols

Preparation and Reactions of Thiols

Thiols are prepared using the hydrosulfide anion as a nucleophile in a nucleophilic substitution reaction with alkyl halides. For instance, bromobutane reacts with sodium hydrosulfide to give butanethiol.

Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide

Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide

Alkenes are converted to 1,2-diols or glycols through a process called dihydroxylation. It involves the addition of two hydroxyl groups across the double bond with two different stereochemical approaches, namely anti and syn. Dihydroxylation using osmium tetroxide progresses with syn stereochemistry.

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Updated: Aug 4, 2025

Protocol for the Solid-phase Synthesis of Oligomers of RNA Containing a 2'-O-thiophenylmethyl Modification and Characterization via Circular Dichroism

Protocol for the Solid-phase Synthesis of Oligomers of RNA Containing a 2'-O-thiophenylmethyl Modification and Characterization via Circular Dichroism

Published on: July 28, 2017

Automated Solid-Phase Oligo(disulfide) Synthesis.

Martin Frandsen¹, Kassem El-Chami¹, Johan Palmfeldt²

¹Department of Chemistry and Interdisciplinary Nanoscience Centre (iNANO), Aarhus University, Gustav Wieds Vej 14, 8000, Aarhus, Denmark.

Angewandte Chemie (International Ed. in English)

|April 2, 2023

Summary

Automated solid-phase synthesis of oligo(disulfide)s was developed using a novel synthetic cycle. These disulfide oligomers show potential for drug delivery systems due to their controlled release capabilities.

Keywords:

Automated Synthesis Cargo Release Disulfides Oligomers Solid-Phase Synthesis

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Last Updated: Aug 4, 2025

Protocol for the Solid-phase Synthesis of Oligomers of RNA Containing a 2'-O-thiophenylmethyl Modification and Characterization via Circular Dichroism

Protocol for the Solid-phase Synthesis of Oligomers of RNA Containing a 2'-O-thiophenylmethyl Modification and Characterization via Circular Dichroism

Published on: July 28, 2017

Synthesis of Information-bearing Peptoids and their Sequence-directed Dynamic Covalent Self-assembly

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Published on: February 6, 2020

Synthesis of a Water-soluble Metal–Organic Complex Array

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Published on: October 8, 2016

Area of Science:

Chemical Synthesis
Polymer Chemistry
Biotechnology

Background:

Oligo(disulfide)s are versatile molecules with potential applications in various fields.
Developing efficient and automated methods for synthesizing oligo(disulfide)s is crucial for their broader utilization.

Purpose of the Study:

To develop an automated solid-phase synthesis method for oligo(disulfide)s.
To explore the potential of these synthesized molecules in drug delivery applications.

Main Methods:

A synthetic cycle involving deprotection of resin-bound thiols and reaction with thiosulfonate monomers was employed.
Oligo(disulfide)s were synthesized as extensions of oligonucleotides on an automated synthesizer for simplified purification and characterization.
Six dithiol monomer building blocks were synthesized and characterized.

Main Results:

Sequence-defined oligo(disulfide)s with up to seven disulfide units were successfully synthesized and purified.
Tandem MS/MS analysis confirmed the sequence of the synthesized oligomers.
A coumarin-containing monomer was incorporated, and its thiol-mediated release was demonstrated under near-physiological conditions.

Conclusions:

The developed method enables automated and efficient synthesis of oligo(disulfide)s.
The synthesized oligo(disulfide)s exhibit potential for controlled cargo release, highlighting their utility in drug delivery systems.