Improvement of the stereoselectivity of the glycosylation reaction with 2-azido-2-deoxy-1-thioglucoside donors

•A 6-O-chloroacetyl group on the thioglucopyranoside afforded higher α-selectivity.•Several structural distinct acceptors were used.•The nature of the acceptor was found to be critical to the stereoselectivity. 2-Azido-2-deoxy-1-thioglucoside donors with an electron withdrawing group at position 6 w...

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Bibliographic Details
Published in:Carbohydrate research 2016-05, Vol.426, p.33-39
Main Authors: Lourenço, E.C., Ventura, M.R.
Format: Article
Language:English
Subjects:
1,2-cis Glycosides
2-Azido-2-deoxy-1-thioglucosides
Alcohols - chemistry
Carbohydrate Conformation
Carbohydrates - chemistry
Glycosylation
Glycosylation reaction
Stereoisomerism
Steroids - chemistry
Thioglucosides - chemistry
α-2-Azido-2-deoxy-glucosides
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Summary:•A 6-O-chloroacetyl group on the thioglucopyranoside afforded higher α-selectivity.•Several structural distinct acceptors were used.•The nature of the acceptor was found to be critical to the stereoselectivity. 2-Azido-2-deoxy-1-thioglucoside donors with an electron withdrawing group at position 6 were employed to study the stereoselectivity of the glycosylation reaction with several acceptors, ranging from unhindered small primary alcohols to other sugars and steroids, using NIS/TfOH as promoter. p-Tolyl 2-azido-3,4-di-O-benzyl-6-O-chloroacetyl-2-deoxy-1-thio-α/β-D-glucopyranoside afforded the higher α-selectivity, showing that a stronger electron withdrawing ester at O-6 influenced the anomeric selectivity towards the 1,2-cis glucosides. The anomeric stereoselectivity was highly dependent on the acceptor.
ISSN:0008-6215
1873-426X
DOI:10.1016/j.carres.2016.03.021