Literature DB >> 19247426

Imposing the trans/gauche conformation on a sialic acid donor with a 5-N,7-O-oxazinanone group: effect on glycosylation stereoselectivity.

David Crich1, Baolin Wu.   

Abstract

A 5-N,7-O-oxazinanone derivative of a thiosialic acid ester has been synthesized and investigated for the effect of conformational restriction on glycosylation. The cyclic group is found to be powerfully disarming, but to have no beneficial effect on reaction stereoselectivity.

Entities:  

Year:  2008        PMID： 19247426      PMCID： PMC2494599          DOI： 10.1016/j.tet.2007.12.026

Source DB:  PubMed          Journal:  Tetrahedron        ISSN： 0040-4020            Impact factor:   2.457


  23 in total

1.  Chemoselective Iterative Dehydrative Glycosylation This research was supported by the National Institutes of Health (Grant no.: GM-58833), the Arnold and Mabel Beckman Foundation (BYI), Glaxo Wellcome Inc., and the Alfred P. Sloan Foundation. D.Y.G. is a Cottrell Scholar of Research Corporation.

Authors:  Hien M. Nguyen; Jennifer L. Poole; David Y. Gin
Journal:  Angew Chem Int Ed Engl       Date:  2001-01-19       Impact factor: 15.336

2.  Recent advances in o-sialylation.

Authors:  G J Boons; A V Demchenko
Journal:  Chem Rev       Date:  2000-12-13       Impact factor: 60.622

3.  Selectinminus signCarbohydrate Interactions: From Natural Ligands to Designed Mimics.

Authors:  Eric E. Simanek; Glenn J. McGarvey; Jill A. Jablonowski; Chi-Huey Wong
Journal:  Chem Rev       Date:  1998-04-02       Impact factor: 60.622

4.  Stereoselective synthesis of oligo-alpha-(2,8)-sialic acids.

Authors:  Hiroshi Tanaka; Yuji Nishiura; Takashi Takahashi
Journal:  J Am Chem Soc       Date:  2006-06-07       Impact factor: 15.419

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.  Chemistry of 4,6-O-Benzylidene-D-glycopyranosyl Triflates: Contrasting Behavior between the Gluco and Manno Series.

Authors:  David Crich; Weiling Cai
Journal:  J Org Chem       Date:  1999-06-25       Impact factor: 4.354

7.  Dehydrative sialylation with C2-hemiketal sialyl donors.

Authors:  Jannine M Haberman; David Y Gin
Journal:  Org Lett       Date:  2003-07-10       Impact factor: 6.005

8.  alpha-selective sialylations at -78 degrees C in nitrile solvents with a 1-adamantanyl thiosialoside.

Authors:  David Crich; Wenju Li
Journal:  J Org Chem       Date:  2007-09-07       Impact factor: 4.354

9.  The 3,4-O-carbonate protecting group as a beta-directing group in rhamnopyranosylation in both homogeneous and heterogeneous glycosylations as compared to the chameleon-like 2,3-O-carbonates.

Authors:  David Crich; A U Vinod; John Picione
Journal:  J Org Chem       Date:  2003-10-31       Impact factor: 4.354

Review 10.  Biological roles of oligosaccharides: all of the theories are correct.

Authors:  A Varki
Journal:  Glycobiology       Date:  1993-04       Impact factor: 4.313
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  6 in total

1.  Total Synthesis of the Aminopropyl Functionalized Ganglioside GM(1).

Authors:  Bin Sun; Bo Yang; Xuefei Huang
Journal:  Sci China Chem       Date:  2012-01-01       Impact factor: 9.445

2.  Methodology development and physical organic chemistry: a powerful combination for the advancement of glycochemistry.

Authors:  David Crich
Journal:  J Org Chem       Date:  2011-10-04       Impact factor: 4.354

3.  Chemoenzymatic Syntheses of Tumor-Associated Carbohydrate Antigen Globo-H and Stage-Specific Embryonic Antigen 4.

Authors:  Zhen Wang; Michel Gilbert; Hironobu Eguchi; Hai Yu; Jiansong Cheng; Saddam Muthana; Luyuan Zhou; Peng George Wang; Xi Chen; Xuefei Huang
Journal:  Adv Synth Catal       Date:  2008-08-04       Impact factor: 5.837

4.  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

5.  Influence of side chain conformation and configuration on glycosyl donor reactivity and selectivity as illustrated by sialic acid donors epimeric at the 7-position.

Authors:  Pavan K Kancharla; David Crich
Journal:  J Am Chem Soc       Date:  2013-12-09       Impact factor: 15.419

Review 6.  Mechanistic Investigations into the Application of Sulfoxides in Carbohydrate Synthesis.

Authors:  Martin A Fascione; Robin Brabham; W Bruce Turnbull
Journal:  Chemistry       Date:  2016-01-07       Impact factor: 5.236
  6 in total

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