Glycochemistry

The following topics will be covered:

- General mechanism of glycosylation

- Synthesis of glycosyl donors

- Methods of activation of glycosyl donors

- Stereoselective synthesis of some natural oligosaccharides

Hourly volumes* :

CM : 15

TD : 5

The objective of this course is to apply the knowledge of glycochemistry acquired in L3 (HAC605C) to modern techniques of synthesis of natural glycosides and oligosaccharides.

Organic chemistry level L3

Final written exam of 2 hours

• Authorized documents: no
• Non-graphic calculator allowed: yes
• Internet allowed : no

Course (15 H): Materials available on ENT (Moodle): Course documents, TD documents, exam annals 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

_SN2type methods

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

TD (5 H): Individual work, exercises to prepare before and during the session.

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

Administrative contact(s):

Secretariat Master Chemistry

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