Literature DB >> 19908913

Functional group tolerance in organocatalytic regioselective acylation of carbohydrates.

Yoshihiro Ueda1, Wataru Muramatsu, Kenji Mishiro, Takumi Furuta, Takeo Kawabata.   

Abstract

Organocatalytic regioselective acylation of mono- and disaccaharides with various functionalized acid anhydrides has been developed. Acylation of octyl beta-D-glucopyranoside with acid anhydrides derived from alpha-amino acids, cinnamic acid, and gallic acid took place at C(4)-OH with 67-94% regioselectivity in the presence of catalyst 1. Regioselective acylation of disaccharides with functionalized acid anhydrides was also achieved with 78-94% selectivity. Especially, a disaccharide with seven free hydroxy groups (X = OH, R' = H) underwent acylation at C(4)-OH with 78% regioselectivity in the presence of 1. Thus, functional group tolerance in the regioselective acylation catalyzed by 1 was found to be high.

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Year:  2009        PMID： 19908913     DOI： 10.1021/jo901569v

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  8 in total

Review 1.  Synthesis of carbohydrate building blocks via regioselective uniform protection/deprotection strategies.

Authors:  Tinghua Wang; Alexei V Demchenko
Journal:  Org Biomol Chem       Date:  2019-05-02       Impact factor: 3.876

Review 2.  Asymmetric Iridium-Catalyzed C-C Coupling of Chiral Diols via Site-Selective Redox-Triggered Carbonyl Addition.

Authors:  Inji Shin; Michael J Krische
Journal:  Top Curr Chem       Date:  2016

3.  Diastereo- and Enantioselective Iridium Catalyzed Coupling of Vinyl Aziridines with Alcohols: Site-Selective Modification of Unprotected Diols and Synthesis of Substituted Piperidines.

Authors:  Gang Wang; Jana Franke; Chinh Q Ngo; Michael J Krische
Journal:  J Am Chem Soc       Date:  2015-06-15       Impact factor: 15.419

Review 4.  Applications of Nonenzymatic Catalysts to the Alteration of Natural Products.

Authors:  Christopher R Shugrue; Scott J Miller
Journal:  Chem Rev       Date:  2017-06-05       Impact factor: 60.622

5.  Catalyst-directed diastereo- and site-selectivity in successive nucleophilic and electrophilic allylations of chiral 1,3-diols: protecting-group-free synthesis of substituted pyrans.

Authors:  Inji Shin; Gang Wang; Michael J Krische
Journal:  Chemistry       Date:  2014-08-28       Impact factor: 5.236

6.  Controlling the Site Selectivity in Acylations of Amphiphilic Diols: Directing the Reaction toward the Apolar Domain in a Model Diol and the Midecamycin A1 Macrolide Antibiotic.

Authors:  Reut Fallek; Natali Ashush; Amit Fallek; Or Fleischer; Moshe Portnoy
Journal:  J Org Chem       Date:  2022-07-08       Impact factor: 4.198

7.  Asymmetric desymmetrization of meso-diols by C(2)-symmetric chiral 4-pyrrolidinopyridines.

Authors:  Hartmut Schedel; Keizo Kan; Yoshihiro Ueda; Kenji Mishiro; Keisuke Yoshida; Takumi Furuta; Takeo Kawabata
Journal:  Beilstein J Org Chem       Date:  2012-10-17       Impact factor: 2.883

8.  Site-Selective Acylations with Tailor-Made Catalysts.

Authors:  Florian Huber; Stefan F Kirsch
Journal:  Chemistry       Date:  2016-03-10       Impact factor: 5.236
  8 in total

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