One-step synthesis of Ling's tetrol and its conversion into A,D-di--α-cyclodextrin derivatives
2 A-F ,3 B,C,E,F ,6 B,C,E,F -Tetradeca- O -benzyl-α-cyclodextrin or Ling's tetrol is a unique α-cyclodextrin derivative that is partially protected with specific access points on both rims of the cyclodextrin structure. Ling's tetrol is therefore potentially useful for the synthesis of mor...
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Published in | Organic & biomolecular chemistry Vol. 21; no. 45; pp. 8993 - 94 |
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Main Authors | , , |
Format | Journal Article |
Published |
22.11.2023
|
Online Access | Get full text |
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Summary: | 2
A-F
,3
B,C,E,F
,6
B,C,E,F
-Tetradeca-
O
-benzyl-α-cyclodextrin or Ling's tetrol is a unique α-cyclodextrin derivative that is partially protected with specific access points on both rims of the cyclodextrin structure. Ling's tetrol is therefore potentially useful for the synthesis of more complex and sophisticated enzyme models and supramolecular structures. However, the original synthesis gave only 10% yield after a reaction time of 4 days, and a recent improvement that gave 52% yield required two steps and a reaction time in one step of 6 days. Here, a single-step synthesis is reported where Ling's tetrol is obtained in a yield of 59% with a reaction time of 40 hours. 2
A-F
,3
B,C,E,F
,6
B,C,E,F
-Tetradeca-
O
-benzyl-α-cyclodextrin was subsequently converted into 6
A,D
-dicarboxy-3
A,D
-di
epi
-α-cyclodextrin, 3
A,D
-dioxo-α-cyclodextrin and 3
A,D
-diamino-3
A,D
-dideoxy-3
A,D
-di
epi
-α-cyclodextrin. The binding of these compounds to CH
4
and CO
2
was determined.
Ling's tetrol was prepared in 59% yield and used in the synthesis of unique cyclodextrin derivatives. |
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Bibliography: | 6-12 12 14 15 6-16 16 and the NMR assignment tables of compounds Electronic supplementary information (ESI) available: NMR spectra of UV/VIS spectra and Benesi-Hildebrand plots used to determine the binding constants of α-CD , and all new compounds 4 to azodyes. See DOI and 8 https://doi.org/10.1039/d3ob01576a |
ISSN: | 1477-0520 1477-0539 |
DOI: | 10.1039/d3ob01576a |