3-(2′,3′,4′-Tri-O-Acetyl-α-l-Fucopyranosyl)-1-Propene

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F60461373%3A22330%2F21%3A43922823" target="_blank" >RIV/60461373:22330/21:43922823 - 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

3-(2′,3′,4′-Tri-O-Acetyl-α-l-Fucopyranosyl)-1-Propene

Popis výsledku v původním jazyce

C-Glycosyl compounds form a small family of natural products with a broad variety of biological activities. C-glycosyl compounds are analogs of O-glycosides with a carbon–carbon bond replacing the enzymatically labile carbon–oxygen anomeric bond. C-Aryl glycosyl compounds are ubiquitous but alkyl derivatives relatively scarce and are less studied. Glycosylation of 6-deoxy-hexoses such as l-rhamnose or l-fucose, especially the 1,2-cis-O-glycosylation, is quite challenging due to difficult stereocontrol of the anomeric bond. C-Allylation of peracetylated fucose 1 has been reported in several studies, but no synthetic procedure was reported. Literature precedence indicated that the use of acetonitrile as solvent in other situations was beneficial for the a-stereoselectivity of C-allylation. Nuclear magnetic resonance (NMR) spectra were recorded in solvents indicated, at 293 K using a Varian Inova 600 MHz NMR system equipped with a HCN triple resonance cold probe.

Název v anglickém jazyce

3-(2′,3′,4′-Tri-O-Acetyl-α-l-Fucopyranosyl)-1-Propene

Popis výsledku anglicky

C-Glycosyl compounds form a small family of natural products with a broad variety of biological activities. C-glycosyl compounds are analogs of O-glycosides with a carbon–carbon bond replacing the enzymatically labile carbon–oxygen anomeric bond. C-Aryl glycosyl compounds are ubiquitous but alkyl derivatives relatively scarce and are less studied. Glycosylation of 6-deoxy-hexoses such as l-rhamnose or l-fucose, especially the 1,2-cis-O-glycosylation, is quite challenging due to difficult stereocontrol of the anomeric bond. C-Allylation of peracetylated fucose 1 has been reported in several studies, but no synthetic procedure was reported. Literature precedence indicated that the use of acetonitrile as solvent in other situations was beneficial for the a-stereoselectivity of C-allylation. Nuclear magnetic resonance (NMR) spectra were recorded in solvents indicated, at 293 K using a Varian Inova 600 MHz NMR system equipped with a HCN triple resonance cold probe.

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

10

Strana od-do

153-162

Počet stran knihy

344

Název nakladatele

CRC Press, Taylor and Francis Group

Místo vydání

Boca Raton

Kód UT WoS kapitoly

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