Literature DB >> 18440500

Indium triflate catalyzed peracetylation of carbohydrates.

Nicholas P Bizier1, Shannon R Atkins, Luke C Helland, Shane F Colvin, Joseph R Twitchell, Mary J Cloninger.   

Abstract

Peracetylation is a very common protection strategy that is widely implemented in carbohydrate synthesis. Here, a method for the peracetylation of carbohydrates using catalytic In(OTf)(3) in neat acetic anhydride is reported. In(OTf)(3) has low toxicity and is mild and water tolerant, and the reactions are high yielding and efficient. Details regarding the scope and mechanism of the reaction are briefly discussed.

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Year:  2008        PMID： 18440500      PMCID： PMC2494940          DOI： 10.1016/j.carres.2008.04.009

Source DB:  PubMed          Journal:  Carbohydr Res        ISSN： 0008-6215            Impact factor:   2.104


  9 in total

1.  Highly Efficient and Versatile Acylation of Alcohols with Bi(OTf)(3) as Catalyst.

Authors: 
Journal:  Angew Chem Int Ed Engl       Date:  2000-08-18       Impact factor: 15.336

2.  Catalytic nucleophilic acyl substitution of anhydrides by amphoteric vanadyl triflate.

Authors:  C T Chen; J H Kuo; C H Li; N B Barhate; S W Hon; T W Li; S D Chao; C C Liu; Y C Li; I H Chang; J S Lin; C J Liu; Y C Chou
Journal:  Org Lett       Date:  2001-11-15       Impact factor: 6.005

3.  HClO4-SiO2 catalyzed per-O-acetylation of carbohydrates.

Authors:  Anup Kumar Misra; Pallavi Tiwari; Soni Kamlesh Madhusudan
Journal:  Carbohydr Res       Date:  2005-02-07       Impact factor: 2.104

4.  Scandium Trifluoromethanesulfonate as an Extremely Active Lewis Acid Catalyst in Acylation of Alcohols with Acid Anhydrides and Mixed Anhydrides.

Authors:  Kazuaki Ishihara; Manabu Kubota; Hideki Kurihara; Hisashi Yamamoto
Journal:  J Org Chem       Date:  1996-07-12       Impact factor: 4.354

5.  Magnesium bistrifluoromethanesulfonimide as a new and efficient acylation catalyst.

Authors:  Asit K Chakraborti; Shivani Shivani
Journal:  J Org Chem       Date:  2006-07-21       Impact factor: 4.354

6.  Highly powerful and practical acylation of alcohols with acid anhydride catalyzed by Bi(OTf)(3).

Authors:  A Orita; C Tanahashi; A Kakuda; J Otera
Journal:  J Org Chem       Date:  2001-12-28       Impact factor: 4.354

7.  A selective Sc(OTf)3-catalyzed trialkylsilyl ether to acetyl ester exchange reaction with beta-l-idopyranoside and 3,4-O-isopropylidene-beta-D-galactopyranoside derivatives.

Authors:  Weijun Ke; Dennis M Whitfield
Journal:  Carbohydr Res       Date:  2004-12-27       Impact factor: 2.104

8.  InCl3 as a powerful catalyst for the acetylation of carbohydrate alcohols under microwave irradiation.

Authors:  Saibal Kumar Das; K Anantha Reddy; V L Narasimha Rao Krovvidi; K Mukkanti
Journal:  Carbohydr Res       Date:  2005-05-23       Impact factor: 2.104

9.  Facile Cu(OTf)2-catalyzed preparation of per-O-acetylated hexopyranoses with stoichiometric acetic anhydride and sequential one-pot anomeric substitution to thioglycosides under solvent-free conditions.

Authors:  Cheng-An Tai; Suvarn S Kulkarni; Shang-Cheng Hung
Journal:  J Org Chem       Date:  2003-10-31       Impact factor: 4.354
  9 in total
  3 in total

1.  Using In(III) as a promoter for glycosylation.

Authors:  Amanda L Mattson; Anna K Michel; Mary J Cloninger
Journal:  Carbohydr Res       Date:  2011-10-17       Impact factor: 2.104

2.  Nanoparticles To Study Lectins in Caenorhabditis elegans: Multivalent Galactose β1-4 Fucose-Functionalized Dendrimers Provide Protection from Oxidative Stress.

Authors:  Harrison W VanKoten; Rebecca S Moore; Mary J Cloninger
Journal:  Biomacromolecules       Date:  2021-10-27       Impact factor: 6.988

3.  Preparation of dendritic carboranyl glycoconjugates as potential anticancer therapeutics.

Authors:  Biswa Ranjan Swain; Chandra Sekhara Mahanta; Bibhuti Bhusan Jena; Swaraj Kumar Beriha; Bismita Nayak; Rashmirekha Satapathy; Barada P Dash
Journal:  RSC Adv       Date:  2020-09-18       Impact factor: 4.036
  3 in total

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