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Programmed Synthesis of Hepta‐Differentiated β‐Cyclodextrin: 1 out of 117655 Arrangements
Author(s) -
Liu Jiang,
Wang Bo,
Przybylski Cédric,
BistriAslanoff Olivia,
Ménand Mickaël,
Zhang Yongmin,
Sollogoub Matthieu
Publication year - 2021
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.202102182
Subject(s) - surface modification , dendrimer , cyclodextrin , holy grail , chemistry , combinatorial chemistry , regioselectivity , toolbox , nanotechnology , materials science , computer science , organic chemistry , catalysis , world wide web , programming language
Cyclodextrin poly‐functionalization has fueled progress in their use in multiple applications such as enzyme mimicry, but also in the polymer sciences, luminescence, as sensors or for biomedical applications. However, regioselective access to a given pattern of functions on β‐cyclodextrin is still very limited. We uncover a new orienting group, the thioacetate, that expands the toolbox available for cyclodextrin poly‐hetero‐functionalization using diisobutylaluminum hydride (DIBAL‐H) promoted debenzylation. The usefulness of this group is illustrated in the first synthesis of a precisely hepta‐hetero‐functionalized β‐cyclodextrin. By way of comparison, a random hepta‐functionalization would give 117655 different molecules. This synthesis is not simply the vain quest for the Holy Grail of CD hetero‐functionalization, but it illustrates the versatility of the DIBAL‐H oriented hetero‐functionalization strategy, opening the way to a multitude of useful functionalization patterns for new practical applications.