Glycochemistry

The following topics will be covered:

- General mechanism of glycosylation

- Glycosyl donor synthesis

- Glycosyl donor activation methods

- Stereoselective synthesis of some natural oligosaccharides

Hourly volumes* :

CM: 15

TD : 5

The aim of this course is to apply the knowledge of glycochemistry acquired in L3 (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-graphic calculator allowed: yes
• Internet allowed: no

Courses (15 H): Materials available on ENT (Moodle): Course documents, TD documents, exam annals and reference publications.

1. Glycosylation mechanism: (3H)

structure and conformation of intermediates and transition states

using a participating group

use of participating and non-participating solvents

effect of temperature

_SN2methods

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 cations

1. Synthesis of natural oligosaccharides: (3H)

blood group determinants

tetrasaccharide sialyl-Lewis X

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

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

Administrative contact(s) :

Secretariat Master Chemistry

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