Literature DB >> 25382259

Site-selective hexa-hetero-functionalization of α-cyclodextrin an archetypical C₆-symmetric concave cycle.

Bo Wang1, Elena Zaborova1, Samuel Guieu1, Marta Petrillo1, Maxime Guitet1, Yves Blériot2, Mickaël Ménand1, Yongmin Zhang1, Matthieu Sollogoub1.   

Abstract

Access to Cn (n>4) symmetric cyclic concave molecules with a different function on each of their n subunits is an unmet challenge. The reason lies in the lack of a post-functionalization method whose site selectivity is sufficiently understood, predictable and modulable to access most functionalization patterns. Here we disclose a new site-directing rule for a debenzylation reaction on cyclodextrins that solves this problem and allows the unprecedented access to penta- and ultimately hexa-differentiations of such C6 concave cycles. This achievement opens the access to objects with very high-density information.

Entities:  

Year:  2014        PMID: 25382259     DOI: 10.1038/ncomms6354

Source DB:  PubMed          Journal:  Nat Commun        ISSN: 2041-1723            Impact factor:   14.919


  5 in total

1.  Smart regioselectivity towards mono 6-hydroxyl α-cyclodextrin amphiphilic derivatives.

Authors:  Yanli Cui; Yangyi Mao; Jianwei Mao; Yongmin Zhang
Journal:  RSC Adv       Date:  2020-03-13       Impact factor: 4.036

2.  Superstructures with cyclodextrins: Chemistry and applications II.

Authors:  Gerhard Wenz
Journal:  Beilstein J Org Chem       Date:  2015-02-18       Impact factor: 2.883

3.  Qualitative evaluation of regioselectivity in the formation of di- and tri-6-O-tritylates of α-cyclodextrin.

Authors:  Keisuke Yoshikiyo; Yoshihisa Matsui; Tatsuyuki Yamamoto
Journal:  Beilstein J Org Chem       Date:  2015-09-02       Impact factor: 2.883

4.  Direct and Regioselective Di-α-fucosylation on the Secondary Rim of β-Cyclodextrin.

Authors:  Stella A Verkhnyatskaya; Alex H de Vries; Elmatine Douma-de Vries; Renze J L Sneep; Marthe T C Walvoort
Journal:  Chemistry       Date:  2019-03-21       Impact factor: 5.236

5.  Superstructures with cyclodextrins: Chemistry and applications IV.

Authors:  Gerhard Wenz
Journal:  Beilstein J Org Chem       Date:  2017-10-18       Impact factor: 2.883

  5 in total

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