Glycochemistry

The following topics will be covered:

- General Mechanism of Glycosylation

- Synthesis of glycosyl donors

- Methods for Activating Glycosyl Donors

- Stereoselective synthesis of several natural oligosaccharides

Hourly Volumes*:

CM: 15

TD: 5

The objective of this course is to apply the knowledge of glycochemistry acquired in the third year (HAC605C) to modern techniques for the synthesis of natural glycosides and oligosaccharides.

Organic Chemistry (L3 Level)

2-hour written final exam

• Authorized documents: No
• Non-graphical calculators allowed: yes
• Internet access allowed: No

Course (15 hours): Materials available on the digital learning platform (Moodle): Course materials, tutorial materials, past exam papers, and reference publications.

1. Mechanism of glycosylation: (3H)

Structure and Conformation of Intermediates and Transition States

Use of a participating group

Use of participating and non-participating solvents

effect of temperature

_SN2-type reactions

1. Glycosyl donors: (6H)

halides

trichloroacetimidates

phosphites and phosphates

pentenyl glycosides

xanthates

thioglycosides

1. Activation of glycosyl donors: (3H)

Lewis acids

alkylating agents

metal salts

radical reactions

1. Synthesis of Natural Oligosaccharides: (3H)

blood group determinants

sialyl-Lewis X tetrasaccharide

TD (5 hours): Individual work; exercises to be prepared before and during the session.

Exercises on the chemical compatibility between glycosyl donors and acceptors during glycosylation. Exercises on the selection of the activator. Exercises on the stereochemical control of glycosidic couplings.

Administrative contact(s):

Master's in Chemistry Office

https://master-chimie.edu.umontpellier.fr/