Literature DB >> 20527789

Comparison of the armed/disarmed building blocks of the D-gluco and D-glucosamino series in the context of chemoselective oligosaccharide synthesis.

Teerada Kamkhachorn1, Archana R Parameswar, Alexei V Demchenko.   

Abstract

A very elegant Fraser-Reid armed-disarmed approach recently expanded to the building blocks of the superarmed and superdisarmed series shows very high utility in chemoselective oligosaccharide synthesis. Although a number of studies dedicated to the chemoselective activation of 2-amino-2-deoxysugars have emerged, little remains known about how the reactivity of the armed/disarmed building blocks of the neutral sugars directly compares to that of their 2-aminosugar counterparts. A preliminary study of this comparative reactivity is presented.

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Year:  2010        PMID: 20527789      PMCID: PMC2895165          DOI: 10.1021/ol101089u

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  17 in total

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Authors:  Thomas K Ritter; Kwok-Kong T Mong; Haitian Liu; Takuji Nakatani; Chi-Huey Wong
Journal:  Angew Chem Int Ed Engl       Date:  2003-10-06       Impact factor: 15.336

2.  Iterative one-pot synthesis of oligosaccharides.

Authors:  Xuefei Huang; Lijun Huang; Haisheng Wang; Xin-Shan Ye
Journal:  Angew Chem Int Ed Engl       Date:  2004-10-04       Impact factor: 15.336

3.  S-thiazolinyl (STaz) glycosides as versatile building blocks for convergent selective, chemoselective, and orthogonal oligosaccharide synthesis.

Authors:  Papapida Pornsuriyasak; Alexei V Demchenko
Journal:  Chemistry       Date:  2006-08-25       Impact factor: 5.236

4.  Revisiting the armed-disarmed concept rationale: s-benzoxazolyl glycosides in chemoselective oligosaccharide synthesis.

Authors:  Medha N Kamat; Alexei V Demchenko
Journal:  Org Lett       Date:  2005-07-21       Impact factor: 6.005

5.  One-pot synthesis of glucosamine oligosaccharides.

Authors:  Micha Fridman; Dmitry Solomon; Shay Yogev; Timor Baasov
Journal:  Org Lett       Date:  2002-01-24       Impact factor: 6.005

6.  Anomeric reactivity-based one-pot oligosaccharide synthesis: a rapid route to oligosaccharide libraries.

Authors:  X S Ye; C H Wong
Journal:  J Org Chem       Date:  2000-04-21       Impact factor: 4.354

7.  N-trichloroethoxycarbonyl-glucosamine derivatives as glycosyl donors.

Authors:  W Dullenkopf; J C Castro-Palomino; L Manzoni; R R Schmidt
Journal:  Carbohydr Res       Date:  1996-12-24       Impact factor: 2.104

Review 8.  Recent trends in the synthesis of O-glycosides of 2-amino-2-deoxysugars.

Authors:  Aileen F G Bongat; Alexei V Demchenko
Journal:  Carbohydr Res       Date:  2006-10-27       Impact factor: 2.104

9.  Glycosylation with N-Troc-protected glycosyl donors.

Authors:  U Ellervik; G Magnusson
Journal:  Carbohydr Res       Date:  1996-01-11       Impact factor: 2.104

10.  Superarming common glycosyl donors by simple 2-O-benzoyl-3,4,6-tri-O-benzyl protection.

Authors:  Hemali D Premathilake; Laurel K Mydock; Alexei V Demchenko
Journal:  J Org Chem       Date:  2010-02-19       Impact factor: 4.354

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  6 in total

1.  Stereoselectivity of Conformationally Restricted Glucosazide Donors.

Authors:  Stefan van der Vorm; Herman S Overkleeft; Gijsbert A van der Marel; Jeroen D C Codée
Journal:  J Org Chem       Date:  2017-04-25       Impact factor: 4.354

2.  Direct synthesis of diastereomerically pure glycosyl sulfonium salts.

Authors:  Laurel K Mydock; Medha N Kamat; Alexei V Demchenko
Journal:  Org Lett       Date:  2011-05-12       Impact factor: 6.005

Review 3.  Superarmed and superdisarmed building blocks in expeditious oligosaccharide synthesis.

Authors:  Hemali D Premathilake; Alexei V Demchenko
Journal:  Top Curr Chem       Date:  2011

4.  Glycosyl Thioimidates as Versatile Building Blocks for Organic Synthesis.

Authors:  S J Hasty; A V Demchenko
Journal:  Chem Heterocycl Compd (N Y)       Date:  2012-04       Impact factor: 1.277

5.  A Highly Efficient Glycosidation of Glycosyl Chlorides by Using Cooperative Silver(I) Oxide-Triflic Acid Catalysis.

Authors:  Scott A Geringer; Yashapal Singh; Daniel J Hoard; Alexei V Demchenko
Journal:  Chemistry       Date:  2020-06-02       Impact factor: 5.236

Review 6.  Silyl-protective groups influencing the reactivity and selectivity in glycosylations.

Authors:  Mikael Bols; Christian Marcus Pedersen
Journal:  Beilstein J Org Chem       Date:  2017-01-16       Impact factor: 2.883

  6 in total

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