Synthesis of All Configurational Isomers of 1,6-Anhydro-2,3,4-trideoxy-2,3-epimino-4-fluoro-beta-D-hexopyranoses

Result code in IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216208%3A11310%2F10%3A10057088" target="_blank" >RIV/00216208:11310/10:10057088 - 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

Synthesis of All Configurational Isomers of 1,6-Anhydro-2,3,4-trideoxy-2,3-epimino-4-fluoro-beta-D-hexopyranoses

Original language description

Fluorinated hexopyranoses are important synthetic targets because of their utilization as probes in enzymology, medicine and structure - reactivity studies. We have prepared a full series of 1,6-anhydro-2,3,4-deoxy-4-fluoro-2,3-epimino-beta-D-hexopyranoses. The key step was reaction of trans-2,3-azidosulfonates possessing a free C-4 hydroxyl with DAST and subsequent LiAlH4 reduction. Nucleophilic displacement of the hydroxyl activated by DAST proceeded without rearrangement and with moderate to good yields. A convenient synthesis of D-manno epimine from a readily available 3-benzylamino derivative was also developed.

Czech name

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Czech description

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Type

J_x - Unclassified - Peer-reviewed scientific article (Jimp, Jsc and Jost)

CEP classification

CF - Physical chemistry and theoretical chemistry

OECD FORD branch

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Project

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Continuities

Z - Vyzkumny zamer (s odkazem do CEZ)

Publication year

2010

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

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Volume of the periodical

75

Issue of the periodical within the volume

10

Country of publishing house

US - UNITED STATES

Number of pages

4

Pages from-to

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UT code for WoS article

000277531200033

EID of the result in the Scopus database

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