Control of alpha/beta Anomer Formation by a 2',5' Bridge: Toward Nucleoside Derivatives Locked in the South Conformation

Result code in IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61388963%3A_____%2F17%3A00482595" target="_blank" >RIV/61388963:_____/17:00482595 - isvavai.cz</a>

Result on the web

<a href="http://dx.doi.org/10.1021/acs.joc.7b01000" target="_blank" >http://dx.doi.org/10.1021/acs.joc.7b01000</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1021/acs.joc.7b01000" target="_blank" >10.1021/acs.joc.7b01000</a>

Result language

angličtina

Original language name

Control of alpha/beta Anomer Formation by a 2',5' Bridge: Toward Nucleoside Derivatives Locked in the South Conformation

Original language description

We describe a novel stereoselective synthesis of nucleoside derivatives with the ribose ring locked in the South conformation by a bridge between C2' and CS'. Despite the intrinsic constraints of the bicyclic structure, we demonstrate that their synthesis can be achieved by ring closing metathesis of readily accessible precursors. The obtained ribose derivatives are, however, very poor substrates for further installation of the nucleobases, and even simple nucleophiles, such as azido or cyano anions, react with unexpected stereo- or regioselectivity under standard glycosylation conditions. Here we explain this behavior by employing density functional theory (DFT) computations and devise an alternative approach resulting in isomers with the desired orientation of the nucleobase.

Czech name

—

Czech description

—

Type

J_imp - Article in a specialist periodical, which is included in the Web of Science database

CEP classification

—

OECD FORD branch

10401 - Organic chemistry

Project

<a href="/en/project/GA16-20054S" target="_blank" >GA16-20054S: Advanced studies on West Nile virus infection pathogenesis towards novel therapeutic strategies</a><br>

Continuities

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

Publication year

2017

Confidentiality

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

Name of the periodical

Journal of Organic Chemistry

ISSN

0022-3263

e-ISSN

—

Volume of the periodical

82

Issue of the periodical within the volume

21

Country of publishing house

US - UNITED STATES

Number of pages

11

Pages from-to

11337-11347

UT code for WoS article

000414724000003

EID of the result in the Scopus database

2-s2.0-85032793790