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CC BY-ND-NC 4.0 · Synthesis 2019; 51(05): 1196-1206
DOI: 10.1055/s-0037-1611656
DOI: 10.1055/s-0037-1611656
feature
GlucoSiFA and LactoSiFA: New Types of Carbohydrate-Tagged Silicon-Based Fluoride Acceptors for 18F-Positron Emission Tomography (PET)
Natural Sciences and Engineering Research Council of Canada (NSERC) research grant to R.S.Further Information
Publication History
Received: 11 December 2018
Accepted: 17 December 2018
Publication Date:
24 January 2019 (online)
Published as part of the 50 Years SYNTHESIS – Golden Anniversary Issue
Abstract
GlucoSiFA derivatives bearing an azide or alkynyl side chain were obtained from peracetyl-d-glucose using as key step a tosylate substitution by a SiFA thiolate obtained from 4-(di-tert-butylfluorsilyl)benzenethiol. In analogy, two-fold SiFA-substituted maltose and lactose derivatives were synthesized via bistosylates. Introduction of an acetal-protecting group in β-d-azidolactose allowed the synthesis of a LactoSiFA derivative bearing only one SiFA moiety.
Key words
carbohydrates - silicon-based fluoride acceptors - nucleophilic substitution - tosylation - regioselectivitySupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1611656.
- Supporting Information
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