Details

Autor(en) / Beteiligte

• Ghosh, Bhaswati
• Kulkarni, Suvarn S.

Titel

Advances in Protecting Groups for Oligosaccharide Synthesis

Ist Teil von

• Chemistry, an Asian journal, 2020-02, Vol.15 (4), p.450-462

Ort / Verlag

Germany: Wiley Subscription Services, Inc

Erscheinungsjahr

2020

Link zum Volltext

Quelle

MEDLINE

Beschreibungen/Notizen

• Carbohydrates contain numerous hydroxyl groups and sometimes amine functionalities which lead to a variety of complex structures. In order to discriminate each hydroxyl group for the synthesis of complex oligosaccharides, protecting group manipulations are essential. Although the primary role of a protecting group is to temporarily mask a particular hydroxyl/amino group, it plays a greater role in tuning the reactivity of coupling partners as well as regioselectivity and stereoselectivity of glycosylations. Several protecting groups offer anchimeric assistance in glycosylation. They also alter the solubility of substrates and thereby influence the reaction outcome. Since oligosaccharides comprise branched structures, the glycosyl donors and acceptors need to be protected with orthogonal protected groups that can be selectively removed one at a time without affecting other groups. This minireview is therefore intended to provide a discussion on new protecting groups for amino and hydroxyl groups, which have been introduced over last ten years in the field of carbohydrate synthesis. These protecting groups are also useful for synthesizing non‐carbohydrate target molecules as well. High in carbohydrates: In this Minireview, newly introduced protecting groups which are very useful for the synthesis of complex natural products, especially carbohydrates, are discussed. These protecting groups can be easily introduced and selectively removed without affecting other protecting groups. More importantly, they alter the electronic properties of carbohydrate building blocks and control the stereoselectivity of glycosylation by direct participation.