Literature DB >> 11796070

One-pot synthesis of glucosamine oligosaccharides.

Micha Fridman1, Dmitry Solomon, Shay Yogev, Timor Baasov.   

Abstract

[reaction: see text] Tuning the reactivity of glycosyl donors derived from 2-amino-2-deoxy glucose by selective introduction of different N-protecting (NPhth and NHTroc) and anomeric leaving groups (ethylthio and phenylthio) enabled highly efficient oligosaccharide synthesis in a one-pot manner. One-pot sequential glycosylation of three and four units of 2-amino-2-deoxy glucose gave trisaccharides and tetrasaccharide in 50-81% yields.

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Year:  2002        PMID： 11796070     DOI： 10.1021/ol017054d

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


  10 in total

1.  Chemoselective synthesis of oligosaccharides of 2-deoxy-2-aminosugars.

Authors:  Aileen F G Bongat; Medha N Kamat; Alexei V Demchenko
Journal:  J Org Chem       Date:  2007-01-25       Impact factor: 4.354

Review 2.  Automated Chemical Oligosaccharide Synthesis: Novel Approach to Traditional Challenges.

Authors:  Matteo Panza; Salvatore G Pistorio; Keith J Stine; Alexei V Demchenko
Journal:  Chem Rev       Date:  2018-06-28       Impact factor: 60.622

3.  Protecting group-free glycoligation by the desulfurative rearrangement of allylic disulfides as a means of assembly of oligosaccharide mimetics.

Authors:  Venkataraman Subramanian; Myriame Moumé-Pymbock; Tianshun Hu; David Crich
Journal:  J Org Chem       Date:  2011-03-23       Impact factor: 4.354

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

Authors:  Teerada Kamkhachorn; Archana R Parameswar; Alexei V Demchenko
Journal:  Org Lett       Date:  2010-07-02       Impact factor: 6.005

5.  Synthesis of β-(1→6)-linked N-acetyl-D-glucosamine oligosaccharide substrates and their hydrolysis by Dispersin B.

Authors:  Anikó Fekete; Anikó Borbás; Gyöngyi Gyémánt; Lili Kandra; Erika Fazekas; Narayanan Ramasubbu; Sándor Antus
Journal:  Carbohydr Res       Date:  2011-03-23       Impact factor: 2.104

Review 6.  Superarmed and superdisarmed building blocks in expeditious oligosaccharide synthesis.

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

Review 7.  Synthesis and Glycosidation of Anomeric Halides: Evolution from Early Studies to Modern Methods of the 21st Century.

Authors:  Yashapal Singh; Scott A Geringer; Alexei V Demchenko
Journal:  Chem Rev       Date:  2022-06-08       Impact factor: 72.087

8.  Thio-arylglycosides with various aglycon para-substituents: a probe for studying chemical glycosylation reactions.

Authors:  Xiaoning Li; Lijun Huang; Xiche Hu; Xuefei Huang
Journal:  Org Biomol Chem       Date:  2008-10-20       Impact factor: 3.876

9.  Reactivity-based one-pot total synthesis of fucose GM1 oligosaccharide: a sialylated antigenic epitope of small-cell lung cancer.

Authors:  Tony Kwok-Kong Mong; Hing-Ken Lee; Sergio G Duron; Chi-Huey Wong
Journal:  Proc Natl Acad Sci U S A       Date:  2003-01-27       Impact factor: 11.205

10.  How the arming participating moieties can broaden the scope of chemoselective oligosaccharide synthesis by allowing the inverse armed-disarmed approach.

Authors:  James T Smoot; Alexei V Demchenko
Journal:  J Org Chem       Date:  2008-10-22       Impact factor: 4.354
  10 in total

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