Preparation of 6-Monohalo-β-cyclodextrin Derivatives with Selectively Methylated Rims via Diazonium Salts
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216208%3A11310%2F23%3A10467000" target="_blank" >RIV/00216208:11310/23:10467000 - isvavai.cz</a>
Result on the web
<a href="https://verso.is.cuni.cz/pub/verso.fpl?fname=obd_publikace_handle&handle=q50cH9eEFJ" target="_blank" >https://verso.is.cuni.cz/pub/verso.fpl?fname=obd_publikace_handle&handle=q50cH9eEFJ</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1021/acsomega.3c01950" target="_blank" >10.1021/acsomega.3c01950</a>
Alternative languages
Result language
angličtina
Original language name
Preparation of 6-Monohalo-β-cyclodextrin Derivatives with Selectively Methylated Rims via Diazonium Salts
Original language description
A series of 6-monohalo (Cl, Br, and I) β-cyclodextrinderivativeswith various types of methylations were synthesized via a diazotization/nucleophilicdisplacement reaction from the corresponding methylated cyclodextrinamines. All four starting compounds (6(A)-amino-6(A)-deoxy derivatives of native β-CD, per-6-O-methyl-, per-2,3-O-methyl-, and per-2,3,6-O-methyl-β-CD) were found to have different reactivitiesunder the same reaction conditions. Unsubstituted and fully per-O-methylatedcyclodextrin amines undergo fast transformation, giving lower yieldsof the monohalogenated product. The selectively methylated cyclodextrinamines react remarkably slower and provide almost complete conversioninto the desired monohalogenated compound. A pure product was, inseveral cases, successfully isolated with simple purification techniques(extraction and precipitation), allowing large-scale preparations.This new method opens the way for preparing poorly investigated monofunctionalizedselectively methylated cyclodextrins.
Czech name
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Czech description
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Classification
Type
J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database
CEP classification
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OECD FORD branch
10401 - Organic chemistry
Result continuities
Project
—
Continuities
S - Specificky vyzkum na vysokych skolach<br>I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace
Others
Publication year
2023
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
ACS Omega
ISSN
2470-1343
e-ISSN
2470-1343
Volume of the periodical
8
Issue of the periodical within the volume
31
Country of publishing house
US - UNITED STATES
Number of pages
9
Pages from-to
28268-28276
UT code for WoS article
001034638100001
EID of the result in the Scopus database
2-s2.0-85167928113