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. 2019 Sep 12;25(51):11831-11836.
doi: 10.1002/chem.201901969. Epub 2019 Aug 20.

Bromine-Promoted Glycosidation of Conformationally Superarmed Thioglycosides

Matteo Panza  1 , Monica Civera  2 , Jagodige P Yasomanee  1 , Laura Belvisi  2 , Alexei V Demchenko  1
Affiliations

Bromine-Promoted Glycosidation of Conformationally Superarmed Thioglycosides

Matteo Panza et al. Chemistry. .

Abstract

Presented herein is a study of the conformation and reactivity of highly reactive thioglycoside donors. The structural studies have been conducted using NMR spectroscopy and computational methods. The reactivity of these donors has been investigated in bromine-promoted glycosylations of aliphatic and sugar alcohols. Swift reaction times, high yields, and respectable 1,2-cis stereoselectivity were observed in a majority of these glycosylations.

Keywords: carbohydrate chemistry; glycosylation; stereocontrolled reactions; synthesis.

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Figures

Figure 1.
Figure 1.
DFT-optimized 3S1 skew-boat conformation of the 3,4-OTIPS thioglucoside β–3 (hydrogens and phenyl groups have been omitted for clarity in the ball and stick 3D-representation).
Figure 2.
Figure 2.
Conformation and stereoselectivity of β-bromides
Scheme 1.
Scheme 1.
Previous glycosidations of thioglycosides with Br2
Scheme 2.
Scheme 2.
Conversion of 3,4-di-O-TBS β-SEt glucoside β–2 into α,β-bromides 4
See this image and copyright information in PMC

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