Jove
Visualize
Contact Us
JoVE
x logofacebook logolinkedin logoyoutube logo
ABOUT JoVE
OverviewLeadershipBlogJoVE Help Center
AUTHORS
Publishing ProcessEditorial BoardScope & PoliciesPeer ReviewFAQSubmit
LIBRARIANS
TestimonialsSubscriptionsAccessResourcesLibrary Advisory BoardFAQ
RESEARCH
JoVE JournalMethods CollectionsJoVE Encyclopedia of ExperimentsArchive
EDUCATION
JoVE CoreJoVE BusinessJoVE Science EducationJoVE Lab ManualFaculty Resource CenterFaculty Site
Terms & Conditions of Use
Privacy Policy
Policies

Related Concept Videos

Protecting Groups for Aldehydes and Ketones: Introduction01:23

Protecting Groups for Aldehydes and Ketones: Introduction

9.2K
Protecting groups are compounds that can bind to a specific functional group in the presence of other functional groups to protect them from undesired chemical reactions. These compounds can selectively bind to particular functional groups and advance chemoselective reactions in polyfunctional systems (Figure 1). After the functional group has served its purpose, it is removed by reacting it with specific compounds.
9.2K
Hydroboration-Oxidation of Alkenes03:08

Hydroboration-Oxidation of Alkenes

11.7K
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.
11.7K
Regioselectivity and Stereochemistry of Hydroboration02:36

Regioselectivity and Stereochemistry of Hydroboration

9.6K
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.
9.6K
Preparation of Alcohols via Addition Reactions02:15

Preparation of Alcohols via Addition Reactions

7.9K
Overview
The acid-catalyzed addition of water to the double bond of alkenes is a large-scale industrial method used to synthesize low-molecular-weight alcohols. An acidic atmosphere is required to allow the hydrogen in the water molecule to act as an electrophile and attack the double bond in an alkene. The addition of a proton to the double bond creates a carbocation intermediate. The proton preferentially bonds to the less substituted end of the double bond to create a more stable carbocation...
7.9K
Protection of Alcohols02:31

Protection of Alcohols

8.1K
This lesson delves into the concept of protection and deprotection of a functional group fundamental to synthetic organic chemistry. These phenomena are explained in the context of aliphatic and aromatic alcohols.
Protection
It defines a protecting group as the masking agent to make the more reactive species inert to a given set of conditions. This concept is depicted via the illustration of liquid flow through different outlets in an assembly of pipes. The analogy helps to understand the role...
8.1K
Alcohols from Carbonyl Compounds: Reduction02:23

Alcohols from Carbonyl Compounds: Reduction

12.6K
Reduction is a simple strategy to convert a carbonyl group to a hydroxyl group. The three major pathways to reduce carbonyls to alcohols are catalytic hydrogenation, hydride reduction, and borane reduction.
Catalytic hydrogenation is similar to the reduction of an alkene or alkyne by adding H2 across the pi bond in the presence of transition metal catalysts like Raney Ni, Pd–C, Pt, or Ru. Aldehydes and ketones can be reduced by this method, often under mild to moderate heat (25–100°C) and...
12.6K

You might also read

Related Articles

Articles linked to this work by shared authors, journal, and citation graph.

Sort by
Same author

Elevated mitochondrial protein import in acute myeloid leukemia increases reliance on mitochondrial protease LONP1.

The Journal of clinical investigation·2026
Same author

Epigenome regulators imbue a single eukaryotic promoter with diverse gene expression dynamics.

iScience·2026
Same author

Context Rules! Special Issue on "Physical Organic Chemistry: Never Out of Style".

The Journal of organic chemistry·2026
Same author

Development of small molecule inhibitors of ECM collagen secretion.

RSC medicinal chemistry·2025
Same author

Regioselective, Lewis Acid-Catalyzed Ring-Openings of 2,3-Aziridyl Alcohols with Azoles.

The Journal of organic chemistry·2025
Same author

Serine phosphorylation facilitates protein degradation by the human mitochondrial ClpXP protease.

Proceedings of the National Academy of Sciences of the United States of America·2025

Related Experiment Video

Updated: Feb 24, 2026

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

9.2K

Sequential Functionalizations of Carbohydrates Enabled by Boronic Esters as Switchable Protective/Activating Groups.

Ross S Mancini1, Jessica B Lee1, Mark S Taylor1

  • 1Department of Chemistry, University of Toronto , Toronto, Ontario M5S 3H6, Canada.

The Journal of Organic Chemistry
|August 18, 2017
PubMed
Summary
This summary is machine-generated.

This study introduces a novel method using boronic esters for site-selective carbohydrate functionalization. This approach simplifies the synthesis of complex sugar derivatives by acting as both a protective and activating group.

More Related Videos

Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy
07:36

Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy

Published on: November 9, 2019

8.5K
High-throughput Synthesis of Carbohydrates and Functionalization of Polyanhydride Nanoparticles
14:37

High-throughput Synthesis of Carbohydrates and Functionalization of Polyanhydride Nanoparticles

Published on: July 6, 2012

11.9K

Related Experiment Videos

Last Updated: Feb 24, 2026

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

9.2K
Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy
07:36

Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy

Published on: November 9, 2019

8.5K
High-throughput Synthesis of Carbohydrates and Functionalization of Polyanhydride Nanoparticles
14:37

High-throughput Synthesis of Carbohydrates and Functionalization of Polyanhydride Nanoparticles

Published on: July 6, 2012

11.9K

Area of Science:

  • Carbohydrate Chemistry
  • Organic Synthesis
  • Protective Group Chemistry

Background:

  • Selective functionalization of carbohydrates is crucial for synthesizing complex glycans and glycoconjugates.
  • Traditional methods often require multiple protection/deprotection steps, increasing complexity and reducing yield.
  • Diol protection in carbohydrate chemistry presents challenges for site-selective modifications.

Purpose of the Study:

  • To develop a novel, operationally simple method for site-selective, sequential functionalization of carbohydrate derivatives.
  • To utilize boronic esters as a versatile protective and activating group for diol moieties.
  • To enable the efficient synthesis of di- and trisaccharide derivatives without intermediate purification.

Main Methods:

  • Employing tricoordinate boronic esters as protective groups for sugar-derived diols.
  • Utilizing Lewis base-mediated activation of tetracoordinate boronic ester adducts.
  • Combining initial functionalization (acylation, alkylation, glycosylation) with subsequent amine-mediated glycosylation of the boronic ester.

Main Results:

  • Demonstrated site-selective functionalization of free hydroxyl groups while the diol is protected.
  • Achieved activation of boron-bound oxygen atoms for subsequent electrophilic attack.
  • Successfully synthesized selectively protected di- and trisaccharide derivatives in a streamlined process.
  • Eliminated the need for intermediate purification steps.

Conclusions:

  • Boronic esters offer a unique Lewis base-triggered switching mechanism from latent to active nucleophile.
  • This method provides an efficient and simplified route to complex carbohydrate structures.
  • The developed strategy advances protective group strategies in carbohydrate chemistry.