One-Step Transformation of Glycals into 1-Iodo Glycals

Kód výsledku v 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>

Výsledek na webu

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DOI - Digital Object Identifier

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Jazyk výsledku

angličtina

Název v původním jazyce

One-Step Transformation of Glycals into 1-Iodo Glycals

Popis výsledku v původním jazyce

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.

Název v anglickém jazyce

One-Step Transformation of Glycals into 1-Iodo Glycals

Popis výsledku anglicky

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.

Druh

C - Kapitola v odborné knize

CEP obor

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OECD FORD obor

10401 - Organic chemistry

Projekt

<a href="/cs/project/GA15-17572S" target="_blank" >GA15-17572S: Glykoklastry kalix[4]aren/C-oligosacharidy pro studium selektivity interakcí s lektiny</a><br>

Návaznosti

P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)

Rok uplatnění

2021

Kód důvěrnosti údajů

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Název knihy nebo sborníku

Carbohydrate Chemistry : Proven Synthetic Methods, Volume 5

ISBN

978-0-8153-6788-8

Počet stran výsledku

6

Strana od-do

11-16

Počet stran knihy

344

Název nakladatele

CRC Press, Taylor and Francis Group

Místo vydání

Boca Raton

Kód UT WoS kapitoly

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