Protective group strategies in carbohydrate and peptide chemistry

Ali, A. (2010)

Doctoral Thesis

Protecting groups play a key role in the synthesis of complex natural products.This holds especially true for the synthesis of oligosaccharides, of which the monomeric carbohydrate building blocks usually contain up to five different hydroxyl functions. The discrimination of these hydroxyl functions requires a careful protecting group strategy and typically involves multistep protocols.This thesis describes the prepartion, installation, their use in the synthesis of stereoselective glycosidic bonds. Although protecting groups primarily function to mask a given functionality on the carbohydrate core, they also have a profound effect on the overall reactivity of a carbohydrate building block and can control the stereochemical outcome of a glycosylation reaction. Furthermore protecting groups can be used to introduce extra functionality on the carbohydrate core, such as visualization and/or purification handles. Fluorous solid phase extraction (FSPE) is an emerging tecnique, in which compounds are seperated on the basis of flourous content. The compound bearing fluorous tags which are difficult to purify by routine methods can easily be purified.

• Protective groups
• Carbohydrates
• Glycosylation
• Regioselectivity
• Stereoselectivity
• B-mannosides
• Fluorous tag
• FSPE
• Orthogonal
• Disaccharides

• All authors: Ali, A.
• Supervisor: Marel, G.A. van der
• Co-supervisor: Filippov, D.V.; Codée, J.D.C.
• Qualification: Doctor (dr.)
• Awarding Institution: Faculty of Science, Leiden University
• Date: 2010-10-20
• Sponsorship: Higher Education Commision of Pakistan (HEC) Leiden Institute of Chemistry (LIC)