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 Experiment Videos

Solid-phase synthesis of beta-mannosides.

David Crich1, Mark Smith

  • 1Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, Illinois 60607-7061, USA. dcrich@uic.edu

Journal of the American Chemical Society
|July 26, 2002
PubMed
Summary
This summary is machine-generated.

Related Concept Videos

You might also read

Related Articles

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

Sort by
Same author

Site-Selective Distal Arylation of Sugars Enabled by Cyclic Acetals.

Journal of the American Chemical Society·2026
Same author

Endocyclic Trisubstituted Hydroxylamine Isosteres of Basic Amines for ADME Modulation and Reduction of hERG Activity.

ACS medicinal chemistry letters·2026
Same author

Synthesis of 3‑<i>C</i>‑Methyl‑d‑Mannopyranoside Derivatives Functionalized at the 3‑Position.

ACS omega·2026
Same author

G1405 Ribosomal Methyltransferase-Driven Antibacterial Resistance Affects the 4,5-Disubstituted-2-deoxystreptamine Class of Aminoglycoside Antibiotics.

JACS Au·2026
Same author

Commonality of Mechanism in Glycoside Hydrolases, Nucleoside Hydrolases, and Phosphorylases: Importance of Side-Chain Conformation Preorganization.

JACS Au·2025
Same author

Mechanism of 3-<i>O</i>-Acyl-Directed α-Mannopyranosylation and Rationalization of the Contrasting Behavior of 3-<i>O</i>-Acyl Glucopyranosyl Donors.

The Journal of organic chemistry·2025
Same journal

A Ni-Mediated Cross-Coupling Approach to Deuterated <sup>18</sup>F- Fluoromethylated (Hetero)arenes.

Journal of the American Chemical Society·2026
Same journal

Efficient Light-Driven CO<sub>2</sub> Capture and Reversible Release Enabled by Metastable Photoacid-Decorated Metal-Organic Frameworks.

Journal of the American Chemical Society·2026
Same journal

In Situ Raman Spectroscopy Reveals the Dynamic Evolution and Ethanol Dependence of SEI Structure in Li-Mediated N<sub>2</sub> Reduction Reaction.

Journal of the American Chemical Society·2026
Same journal

Solvent Esterification and Stoichiometric Control in Ambient-Grown FAPbI<sub>3</sub> Single-Crystal Solar Cells.

Journal of the American Chemical Society·2026
Same journal

Unlocking Azulene Functionalization via Strain-Induced Azulyne Intermediates.

Journal of the American Chemical Society·2026
Same journal

An Oxazine-Locked Covalent Organic Framework by a Tandem Pinner/Schiff Base Reaction for Hydrogen Peroxide Photosynthesis.

Journal of the American Chemical Society·2026
See all related articles

This study describes a new method for synthesizing complex carbohydrates using a polymer-supported mannosyl donor. This approach yields anomerically pure mannosides with high efficiency and diastereoselectivity.

Area of Science:

  • Carbohydrate Chemistry
  • Organic Synthesis
  • Polymer Chemistry

Background:

  • Efficient synthesis of complex carbohydrates is crucial for glycobiology.
  • Developing robust and scalable glycosylation methods remains a challenge.
  • Polymer-supported synthesis offers advantages in purification and reagent recovery.

Purpose of the Study:

  • To develop a novel polymer-supported glycosylation strategy for mannose derivatives.
  • To achieve anomerically pure beta-D-mannopyranosides.
  • To demonstrate the versatility of the method with various glycosyl acceptors.

Main Methods:

  • S-phenyl 2,3-di-O-benzyl-alpha-D-thiomannopyranoside was immobilized on a cross-linked polystyrene support.
  • Polymer-supported mannosyl donor activation using 1-benzenesulfinyl piperidine and trifluoromethanesulfonic anhydride.

Related Experiment Videos

  • Glycosylation performed at low temperature followed by cleavage from the resin.

    • Main Results:

    • Anomerically pure 2,3-di-O-benzyl-beta-D-mannopyranosides were obtained in excellent yields.
    • High diastereoselectivity was achieved in coupling reactions.
    • Successful coupling with primary, secondary, and tertiary glycosyl acceptors, including carbohydrates and threonine derivatives.

    Conclusions:

    • The described polymer-supported method provides an efficient route to beta-D-mannopyranosides.
    • This strategy is applicable to a wide range of glycosyl acceptors.
    • The method holds promise for the synthesis of complex glycoconjugates.