Enhanced single-isomer separation and pseudoenantiomer resolution of new primary rim heterobifunctionalized alpha-cyclodextrin derivatives
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216208%3A11310%2F18%3A10389370" target="_blank" >RIV/00216208:11310/18:10389370 - isvavai.cz</a>
Result on the web
<a href="https://doi.org/10.3762/bjoc.14.261" target="_blank" >https://doi.org/10.3762/bjoc.14.261</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.3762/bjoc.14.261" target="_blank" >10.3762/bjoc.14.261</a>
Alternative languages
Result language
angličtina
Original language name
Enhanced single-isomer separation and pseudoenantiomer resolution of new primary rim heterobifunctionalized alpha-cyclodextrin derivatives
Original language description
The synthesis of batch-to-batch reproducible cyclodextrin (CD) derivatives often requires functionalization at specific positions of the CD skeleton. However, the regioselective preparation of this type of CD derivatives remains a challenge in synthetic chemistry. Thus, the present study aimed to prepare all positional regioisomers on the primary rim of homobifunctionalized diazido-alpha-CDs by selective substitution on the primary rim. Specifically, three positional regioisomers 6(A),6(B)-6(A),6(C), and 6(A),6(D) diazido-alpha-CDs were prepared via different intermediates (using sulfonylation with capping agents, bromination and tosylation). Furthermore, heterobifunctionalized 6(A)-azido-6(x)-mesitylenesulfonyl-alpha-CDs were also synthesized, and all regioisomers were successfully separated by HPLC. Moreover, the heterobifunctionalized alpha-CD regioisomers were isolated in gram-scale quantities, isomers AB and AC in the form of a pseudoenantiomeric mixture. The pseudoenantiomers AC/CA and AB/BA were resolved on an analytical scale by HPLC-MS at 10 degrees C. Thus, the presented synthetic and analytical methods for homo- and heterodisubstituted alpha-CDs are efficient and reproducible for the preparation of various pure regioisomeric CD derivatives. Accordingly, our findings indicate, (i) the versatility of selectively modified azido and mesitylene CD skeletons in preparing new types of alpha-CD derivatives and (ii) the potential of using resolved alpha-CD pseudoenantiomers in other research fields such as organocatalysis.
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
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Continuities
S - Specificky vyzkum na vysokych skolach<br>I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace
Others
Publication year
2018
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
Beilstein Journal of Organic Chemistry
ISSN
1860-5397
e-ISSN
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Volume of the periodical
14
Issue of the periodical within the volume
November
Country of publishing house
DE - GERMANY
Number of pages
9
Pages from-to
2829-2837
UT code for WoS article
000451065200001
EID of the result in the Scopus database
2-s2.0-85056986656