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Synthesis 2024; 56(07): 1147-1156
DOI: 10.1055/a-2183-0175
DOI: 10.1055/a-2183-0175
paper
Emerging Trends in Glycoscience
Expedient Synthesis of Superarmed Glycosyl Donors via Oxidative Thioglycosidation of Glycals
A.V.D. thanks the National Institute of General Medical Sciences (GM111835) and the National Science Foundation (CHE-2147156) for support of this work. N.P.F. was supported by the National Institute of General Medical Sciences (T32, GM141602 grant).
Abstract
Superarmed glycosyl donors have higher reactivity compared to their perbenzylated armed counterparts. Generally, the 2-O-benzoyl-3,4,6-tri-O-benzyl protecting group pattern gives rise to increased reactivity due to an O-2/O-5 cooperative effect. Despite having a high reactivity profile and applicability in many expeditious strategies for glycan synthesis, regioselective introduction of the superarming protecting group pattern is tedious for most sugar series. Reported herein is a streamlined synthetic route to yield superarmed glycosyl donors of the d-gluco and d-galacto series equipped with an ethylthio, phenylthio, p-tolylthio, benzoxazol-2-ylthio, O-allyl, or O-pentenyl anomeric leaving group. This streamlined approach was made possible due to the refinement of the oxidative thioglycosylation reaction of the respective glucal and galactal precursors. The applicability of this approach to the direct formation of disaccharides is also showcased.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2183-0175.
- Supporting Information
Publication History
Received: 08 August 2023
Accepted after revision: 27 September 2023
Accepted Manuscript online:
27 September 2023
Article published online:
31 October 2023
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