TY - JOUR

T1 - One-step synthesis of Ling's tetrol and its conversion into A,D-di-allo-α-cyclodextrin derivatives

AU - Zorck, Waldemar Frederik

AU - Pedersen, Martin Jæger

AU - Bols, Mikael

N1 - Funding Information: 800 MHz NMR data were recorded at cOpenNMR, an infrastructure facility funded by the Novo Nordisk Foundation (#NNF18OC0032996). We also thank the Novo Nordisk Foundation for financial support through the NMR infrastructure grant (NNF21OC0067315) and the project grant (NNF21OC0071886), and the Carlsberg Foundation for the infrastructure grant CF21-0152. Publisher Copyright: © 2023 The Royal Society of Chemistry.

PY - 2023

Y1 - 2023

N2 - 2A-F,3B,C,E,F,6B,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. 2A-F,3B,C,E,F,6B,C,E,F-Tetradeca-O-benzyl-α-cyclodextrin was subsequently converted into 6A,D-dicarboxy-3A,D-diepi-α-cyclodextrin, 3A,D-dioxo-α-cyclodextrin and 3A,D-diamino-3A,D-dideoxy-3A,D-diepi-α-cyclodextrin. The binding of these compounds to CH4 and CO2 was determined.

AB - 2A-F,3B,C,E,F,6B,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. 2A-F,3B,C,E,F,6B,C,E,F-Tetradeca-O-benzyl-α-cyclodextrin was subsequently converted into 6A,D-dicarboxy-3A,D-diepi-α-cyclodextrin, 3A,D-dioxo-α-cyclodextrin and 3A,D-diamino-3A,D-dideoxy-3A,D-diepi-α-cyclodextrin. The binding of these compounds to CH4 and CO2 was determined.

U2 - 10.1039/d3ob01576a

DO - 10.1039/d3ob01576a

M3 - Journal article

C2 - 37869763

AN - SCOPUS:85175478836

VL - 21

SP - 8993

EP - 9004

JO - Organic & Biomolecular Chemistry

JF - Organic & Biomolecular Chemistry

SN - 1470-4358

IS - 45

ER -