Literature DB >> 16442505

Iterative one-pot syntheses of chitotetroses.

Lijun Huang1, Zhen Wang, Xiaoning Li, Xin-shan Ye, Xuefei Huang.   

Abstract

Rapid syntheses of chitotetrose derivatives were achieved in good yields using the newly developed reactivity independent iterative one-pot strategy. The protective groups on donors and acceptors were independently evaluated allowing matching of the two partners in glycosylation. No anomeric reactivity adjustments or intermediate purification were necessary thus significantly improving the overall synthetic efficiency. Only near stoichiometric amounts of building blocks were required for the assembly of target molecules further highlighting the potential of the iterative one-pot method in complex oligosaccharide synthesis.

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Year:  2006        PMID: 16442505      PMCID: PMC1994152          DOI: 10.1016/j.carres.2006.01.007

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


  29 in total

1.  Synthesis of complex carbohydrates and glycoconjugates: enzyme-based and programmable one-pot strategies.

Authors:  K M Koeller; C H Wong
Journal:  Chem Rev       Date:  2000-12-13       Impact factor: 60.622

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.  A four-component one-pot synthesis of alpha-Gal pentasaccharide.

Authors:  Yuhang Wang; Xuefei Huang; Li-He Zhang; Xin-Shan Ye
Journal:  Org Lett       Date:  2004-11-25       Impact factor: 6.005

4.  Intermolecular aglycon transfer of a phenyl 1-thiogalactosaminide derivative under trichloroacetimidate glycosylation conditions.

Authors:  F Belot; J C Jacquinet
Journal:  Carbohydr Res       Date:  1996-08-26       Impact factor: 2.104

5.  Oxazolidinone protection of N-acetylglucosamine confers high reactivity on the 4-hydroxy group in glycosylation.

Authors:  David Crich; A U Vinod
Journal:  Org Lett       Date:  2003-04-17       Impact factor: 6.005

6.  One-pot oligosaccharide synthesis exploiting solvent reactivity effects.

Authors:  M Lahmann; S Oscarson
Journal:  Org Lett       Date:  2000-11-30       Impact factor: 6.005

7.  Stereocontrolled synthesis of chitosan dodecamer.

Authors:  H Kuyama; Y Nakahara; T Nukada; Y Ito; Y Nakahara; T Ogawa
Journal:  Carbohydr Res       Date:  1993-04-23       Impact factor: 2.104

8.  Iterative glycosylation of 2-deoxy-2-aminothioglycosides and its application to the combinatorial synthesis of linear oligoglucosamines.

Authors:  Shigeru Yamago; Takeshi Yamada; Tomokazu Maruyama; Jun-ichi Yoshida
Journal:  Angew Chem Int Ed Engl       Date:  2004-04-13       Impact factor: 15.336

9.  Synthesis of chitooligomer-based glycoconjugates and their binding to the rat natural killer cell activation receptor NKR-P1.

Authors:  T Semenuk; P Krist; J Pavlícek; K Bezouska; M Kuzma; P Novák; V Kren
Journal:  Glycoconj J       Date:  2001-10       Impact factor: 2.916

10.  A novel strategy for oligosaccharide synthesis via temporarily deactivated S-thiazolyl glycosides as glycosyl acceptors.

Authors:  Papapida Pornsuriyasak; Umesh B Gangadharmath; Nigam P Rath; Alexei V Demchenko
Journal:  Org Lett       Date:  2004-11-25       Impact factor: 6.005

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  15 in total

1.  A facile method for oxidation of primary alcohols to carboxylic acids and its application in glycosaminoglycan syntheses.

Authors:  Lijun Huang; Nardos Teumelsan; Xuefei Huang
Journal:  Chemistry       Date:  2006-07-05       Impact factor: 5.236

2.  Synthesis of branched Man5 oligosaccharides and an unusual stereochemical observation.

Authors:  Nardos Teumelsan; Xuefei Huang
Journal:  J Org Chem       Date:  2007-10-16       Impact factor: 4.354

3.  Syntheses of Lewis(x) and dimeric Lewis(x): construction of branched oligosaccharides by a combination of preactivation and reactivity based chemoselective one-pot glycosylations.

Authors:  Adeline Miermont; Youlin Zeng; Yuqing Jing; Xin-shan Ye; Xuefei Huang
Journal:  J Org Chem       Date:  2007-10-16       Impact factor: 4.354

4.  Installation of electron-donating protective groups, a strategy for glycosylating unreactive thioglycosyl acceptors using the preactivation-based glycosylation method.

Authors:  Youlin Zeng; Zhen Wang; Dennis Whitfield; Xuefei Huang
Journal:  J Org Chem       Date:  2008-09-23       Impact factor: 4.354

5.  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

6.  Fluorous-Assisted One-Pot Oligosaccharide Synthesis.

Authors:  Bo Yang; Yuqing Jing; Xuefei Huang
Journal:  European J Org Chem       Date:  2010-01-27

7.  Highly efficient syntheses of hyaluronic acid oligosaccharides.

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

8.  Bis(oxazolines) based on glycopyranosides - steric, configurational and conformational influences on stereoselectivity.

Authors:  Tobias Minuth; Mike M K Boysen
Journal:  Beilstein J Org Chem       Date:  2010-03-04       Impact factor: 2.883

9.  Chemical synthesis of a heparan sulfate glycopeptide: syndecan-1.

Authors:  Bo Yang; Keisuke Yoshida; Zhaojun Yin; Hang Dai; Herbert Kavunja; Mohammad H El-Dakdouki; Suttipun Sungsuwan; Steven B Dulaney; Xuefei Huang
Journal:  Angew Chem Int Ed Engl       Date:  2012-09-07       Impact factor: 15.336

10.  Pre-activation-based one-pot synthesis of an alpha-(2,3)-sialylated core-fucosylated complex type bi-antennary N-glycan dodecasaccharide.

Authors:  Bin Sun; Balasubramanian Srinivasan; Xuefei Huang
Journal:  Chemistry       Date:  2008       Impact factor: 5.236

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