One-Step Transformation of Glycals into 1-Iodo Glycals

Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F60461373%3A22330%2F21%3A43922816" target="_blank" >RIV/60461373:22330/21:43922816 - isvavai.cz</a>
Result on the web
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DOI - Digital Object Identifier
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Result language
angličtina
Original language name
One-Step Transformation of Glycals into 1-Iodo Glycals
Original language description
1-iodo glycals are valuable intermediates for the synthesis of various C-glycosyl compounds using transition-metal catalyzed cross-coupling reactions such as Sonogashira, Stille, and Suzuki reaction or ortho-C–H activation. Preparation and the utilization of 1-iodo-3,4,6-tri-O-TIPS-d-glucal and 1-iodo-3,4,6-tri-O-TIPS-d-galactal were already published,5,6 but some inconveniences continue to exist in their synthesis. This chapter presents an optimized one-pot synthesis of two new 1-iodo glycals, 3 and 4, starting from easily accessible silylated glycals 1 and 2, respectively. For the isolation of 3 and 4 in the purity sufficient for the subsequent cross-coupling reactions, only partition of the reaction mixture between toluene and water is needed, followed by extraction of the organic layer with sodium thiosulfate solution. Pure thin-layer chromatography 1-iodo-glycals3 and 4 are obtained in 76% and 87% yields, respectively.
Czech name
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Czech description
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Project
<a href="/en/project/GA15-17572S" target="_blank" >GA15-17572S: Calix[4]arene/C-oligosaccharide glycoclusters design for improved selectivity of interactions with lectins</a><br>
Continuities
P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)

Publication year
2021
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Book/collection name
Carbohydrate Chemistry : Proven Synthetic Methods, Volume 5
ISBN
978-0-8153-6788-8
Number of pages of the result
6
Pages from-to
11-16
Number of pages of the book
344
Publisher name
CRC Press, Taylor and Francis Group
Place of publication
Boca Raton
UT code for WoS chapter
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