Silylated Sugars – Synthesis and Properties

Abstract

Silicon has been used in carbohydrate chemistry for half a century, but mostly as a protective group for sugar alcohols. Recently, the use of silicon has expanded to functionalization via C–H activation, conformational arming of glycosyl donors, and conformational alteration of carbohydrates. Silicon has proven useful as more than a protective group and during the last one and a half decades we have demonstrated how it influences both the reactivity of glycosyl donors and stereochemical outcome of glycosylations. Silicon can also be attached directly to the sugar C-backbone, which has even more pronounced effects on the chemistry and properties of the molecules. In this Account, we will give a tour through our work involving silicon and carbohydrates.

1 Introduction

2 Conformational Arming of Glycosyl Donors with Silyl Groups

3 Silyl Protective Groups for Tethering Glycosyl Donors

4. Si–C Glycosides via C–H Activation

4.1 C–H Activation and Oxidation of Methyl 6-Deoxy-l-glycosides

4.2 Synthesis of All Eight 6-Deoxy-l-sugars

4.3 Synthesis of All Eight l-Sugars by C–H Activation

4.4 Modification of the Oxasilolane Ring

5 C–Si in Glycosyl Donors – Activating or Not?

6 Si–C-Substituted Pyranosides

7 Perspective

Key words

carbohydrates - silicon - C–H activation - conformation - reactivity - selectivity - glycosylation

Publication History

Received: 27 September 2021

Accepted after revision: 05 October 2021

Article published online:
17 November 2021

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