Literature DB >> 25419207

Regioselective Benzylation of 2-Deoxy-2-Aminosugars Using Crown Ethers: Application to a Shortened Synthesis of Hyaluronic Acid Oligomers.

Chinmoy Mukherjee1, Lin Liu2, Nicola L B Pohl1.   

Abstract

The combination of benzyl bromide, sodium hydroxide and 15-crown-5 in tetrahydrofuran is shown to be an efficient method for installing benzyl groups at both the 4- and 6-positions regioselectively directly from peracetylated N-trichloroacetyl-protected glucosamine and galactosamine. Application of this benzylation strategy proved to significantly shorten the synthetic route to hyaluronic acid tetra- and hexamers.

Entities:  

Keywords:  Benzylation; carbohydrates; phase transfer; protecting groups; trichloroacetyl

Year:  2014        PMID： 25419207      PMCID： PMC4235972          DOI： 10.1002/adsc.201400269

Source DB:  PubMed          Journal:  Adv Synth Catal        ISSN： 1615-4150            Impact factor:   5.837


  44 in total

1.  Regioselective C-3-O-acylation and O-methylation of 4,6-O-benzylidene-beta-D-gluco- and galactopyranosides displaying a range of anomeric substituents.

Authors:  H M Osborn; V A Brome; L M Harwood; W G Suthers
Journal:  Carbohydr Res       Date:  2001-05-18       Impact factor: 2.104

2.  Tandem catalysis for a one-pot regioselective protection of carbohydrates: the example of glucose.

Authors:  Antoine Français; Dominique Urban; Jean-Marie Beau
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

3.  A novel acid-catalyzed O-benzylating reagent with the smallest unit of imidate structure.

Authors:  Kohei Yamada; Hikaru Fujita; Munetaka Kunishima
Journal:  Org Lett       Date:  2012-09-20       Impact factor: 6.005

4.  Iron(III) chloride-tandem catalysis for a one-pot regioselective protection of glycopyranosides.

Authors:  Yann Bourdreux; Aurélie Lemétais; Dominique Urban; Jean-Marie Beau
Journal:  Chem Commun (Camb)       Date:  2011-01-04       Impact factor: 6.222

5.  One-pot synthesis of D-glucosamine and chitobiosyl building blocks catalyzed by triflic acid on molecular sieves.

Authors:  Guillaume Despras; Dominique Urban; Boris Vauzeilles; Jean-Marie Beau
Journal:  Chem Commun (Camb)       Date:  2014-02-04       Impact factor: 6.222

6.  Highly efficient syntheses of hyaluronic acid oligosaccharides.

Authors:  Lijun Huang; Xuefei Huang
Journal:  Chemistry       Date:  2007       Impact factor: 5.236

7.  Automated solid-phase synthesis of hyaluronan oligosaccharides.

Authors:  Marthe T C Walvoort; Anne Geert Volbeda; Niels R M Reintjens; Hans van den Elst; Obadiah J Plante; Herman S Overkleeft; Gijsbert A van der Marel; Jeroen D C Codée
Journal:  Org Lett       Date:  2012-07-10       Impact factor: 6.005

8.  The 1,4-linked disaccharide of hyaluronan: synthesis of methyl 2-acetamido-2-deoxy-beta-D-glucopyranosyl-(1-->4)-beta-D-glucopyrano sid uronic acid.

Authors:  M B Carter; P A Petillo; L Anderson; L E Lerner
Journal:  Carbohydr Res       Date:  1994-05-20       Impact factor: 2.104

9.  Synthesis, characterization and chondroprotective properties of a hyaluronan thioethyl ether derivative.

Authors:  Monica A Serban; Guanghui Yang; Glenn D Prestwich
Journal:  Biomaterials       Date:  2007-12-26       Impact factor: 12.479

Review 10.  Hyaluronidases in cancer biology.

Authors:  Robert Stern
Journal:  Semin Cancer Biol       Date:  2008-04-01       Impact factor: 15.707
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  2 in total

1.  Design and syntheses of hyaluronan oligosaccharide conjugates as inhibitors of CD44-Hyaluronan binding.

Authors:  Xiaowei Lu; Xuefei Huang
Journal:  Glycoconj J       Date:  2015-05-22       Impact factor: 2.916

Review 2.  Synthetic Oligosaccharide Libraries and Microarray Technology: A Powerful Combination for the Success of Current Glycosaminoglycan Interactomics.

Authors:  Vitor H Pomin; Xu Wang
Journal:  ChemMedChem       Date:  2017-12-06       Impact factor: 3.466
  2 in total

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