Literature DB >> 26236049

4-Acetoxy-2,2-dimethylbutanoate: a useful carbohydrate protecting group for the selective formation of β-(1→3)-d-glucans.

Hai Yu1, David L Williams2, Harry E Ensley1.   

Abstract

The use of 4-acetoxy-2,2-dimethylbutanoyl protecting group for the C2-hydroxyl allows the selective formation of β-glycosides without producing α-glycosides. This very bulky protecting group can be removed under mild conditions.

Entities:  

Keywords:  Carbohydrate protecting groups; β-Glucan; β-Glycoside formation

Year:  2005        PMID： 26236049      PMCID： PMC4520321          DOI： 10.1016/j.tetlet.2005.03.099

Source DB:  PubMed          Journal:  Tetrahedron Lett        ISSN： 0040-4039            Impact factor:   2.415


  6 in total

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2.  New Synthetic Methodology for Regio- and Stereoselective Synthesis of Oligosaccharides via Sugar Ortho Ester Intermediates.

Authors:  Wei Wang; Fanzuo Kong
Journal:  J Org Chem       Date:  1998-08-21       Impact factor: 4.354

3.  Immune recognition. A new receptor for beta-glucans.

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Review 4.  Anomeric-oxygen activation for glycoside synthesis: the trichloroacetimidate method.

Authors:  R R Schmidt; W Kinzy
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5.  Synthesis of allyl O-[sodium(alpha-D-glycero-D-talo-2- octulopyranosyl)onate]-(2-->6)-2-acetamido-2-deoxy-beta-D-glucopyranosi de, a core constituent of the lipopolysaccharide from Acinetobacter calcoaceticus NCTC 10305.

Authors:  J Gass; M Strobl; A Loibner; P Kosma; U Zähringer
Journal:  Carbohydr Res       Date:  1993-05-21       Impact factor: 2.104

6.  Remote control of alpha- or beta-stereoselectivity in (1-->3)-glucosylations in the presence of a C-2 ester capable of neighboring-group participation.

Authors:  Ying Zeng; Jun Ning; Fanzuo Kong
Journal:  Carbohydr Res       Date:  2003-02-07       Impact factor: 2.104
  6 in total
  12 in total

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Journal:  Ann Transl Med       Date:  2014-02

Review 2.  Expeditious oligosaccharide synthesis via selective, semi-orthogonal, and orthogonal activation.

Authors:  Sophon Kaeothip; Alexei V Demchenko
Journal:  Carbohydr Res       Date:  2011-05-18       Impact factor: 2.104

3.  Enhanced diastereoselectivity in beta-mannopyranosylation through the use of sterically minimal propargyl ether protecting groups.

Authors:  David Crich; Prasanna Jayalath; Thomas K Hutton
Journal:  J Org Chem       Date:  2006-04-14       Impact factor: 4.354

4.  Synthesis and immunological studies of linear oligosaccharides of β-glucan as antigens for antifungal vaccine development.

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5.  New glucuronic acid donors for the modular synthesis of heparan sulfate oligosaccharides.

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6.  Peridinin Is an Exceptionally Potent and Membrane-Embedded Inhibitor of Bilayer Lipid Peroxidation.

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Journal:  J Am Chem Soc       Date:  2018-11-02       Impact factor: 15.419

7.  Stereocontrolled glycoside and glycosyl ester synthesis. neighboring group participation and hydrogenolysis of 3-(2'-benzyloxyphenyl)-3,3-dimethylpropanoates.

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Review 8.  The Road to Structurally Defined β-Glucans.

Authors:  Patrick Ross; Mark P Farrell
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9.  Synthetic Carbohydrate Chemistry and Translational Medicine.

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10.  Protection against Experimental Melioidosis with a Synthetic manno-Heptopyranose Hexasaccharide Glycoconjugate.

Authors:  Andrew E Scott; William J Christ; Alison J George; Margaret G M Stokes; Gregory J S Lohman; Yuhong Guo; Matthew Jones; Richard W Titball; Timothy P Atkins; A Stewart Campbell; Joann L Prior
Journal:  Bioconjug Chem       Date:  2016-05-17       Impact factor: 4.774
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