Related Experiment Video
Updated: Jan 28, 2026

Detection of Protein S-Acylation using Acyl-Resin Assisted Capture
Published on: April 10, 2020
Stereoselective β-Mannosylation with 2,6-Lactone-bridged Thiomannosyl Donor by Remote Acyl Group Participation
Huanfang Xu1, Long Chen1, Qi Zhang1
1Key Laboratory of Applied Surface and Colloid Chemistry, Shaanxi Normal University, 620 West Chang'an Avenue, Xi'an, Shaanxi, 710119, China.
Abstract:
Stereoselective β-mannosylation has been recognized as one of the greatest challenges of carbohydrate chemistry. Herein, we described a practical method for stereoselective construction of β-mannosides by using a 2,6-lactone-bridged thiomannosyl donor through the remote acyl-group participation as well as the steric effect of O-4 substituent. The two effects are enabled through the conversion of a regular mannopyranosyl 4 C1 conformation into a 2,6-lactone bridged conformation. The lactone donor could be readily prepared in three steps on a gram scale and the β-mannosylation proceeded smoothly with high stereoselectivity for primary, secondary and tertiary alcohol acceptors. In addition, this strategy was successfully applied to the synthesis of a naturally occurring trisaccharide.
More Related Videos
10:17Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones
Published on: February 7, 2019
08:22Remotely Supervised Transcranial Direct Current Stimulation: An Update on Safety and Tolerability
Published on: October 7, 2017
Related Concept Videos
Design Example: Strain Gauge Bridge or Wheatstone Bridge
Bridge rectifier
Operationally, the bridge rectifier allows current flow through two of its diodes during each...
Wheatstone Bridge
Thus, for accurate resistance measurements, a...
Cross-bridge Cycle
Amines to Amides: Acylation of Amines
Next, the second equivalent of amine serves as a Brønsted base and deprotonates the quaternary...
Nucleophilic Acyl Substitution of Carboxylic Acid Derivatives