Glyco-chemistry

The following topics will be covered:

- General mechanism of glycosylation

- Summary of glycosyl donors

- Methods for activating 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 glyco-chemistry acquired in L3 (HAC605C) to modern techniques for synthesizing natural glycosides and oligosaccharides.

Organic Chemistry Level L3

2-hour written final exam

• Authorized documents: no
• Non-graphing calculator permitted: yes
• Internet access: no

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

1. Glycosylation mechanism: (3H)

structure and conformation of intermediates and transition states

use of a participating group

use of solvents participants and non-participants

temperature effect

_SN2-type 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 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 chemical compatibility between glycosyl donors and acceptors during glycosylation. Exercises on choosing the activator. Exercises on stereochemical control of glycosidic couplings.

Administrative contact(s):

Master's Program in Chemistry Secretariat

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