Literature DB >> 18715011

Stereoselective iterative one-pot synthesis of N-glycolylneuraminic acid-containing oligosaccharides.

David Crich1, Baolin Wu.   

Abstract

The use of an N-acyloxazolidinone-protected S-adamantanyl thiosialoside allows the highly stereoselective, one-pot multicomponent synthesis of alpha-sialoside-based oligosaccharides.

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Year:  2008        PMID： 18715011      PMCID： PMC2726932          DOI： 10.1021/ol801548k

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


  12 in total

1.  Recent advances in o-sialylation.

Authors:  G J Boons; A V Demchenko
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.  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

Review 5.  N-Glycolylneuraminic acid in human tumours.

Authors:  Y N Malykh; R Schauer; L Shaw
Journal:  Biochimie       Date:  2001-07       Impact factor: 4.079

6.  Highly efficient syntheses of hyaluronic acid oligosaccharides.

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

7.  O-sialylation with N-acetyl-5-n,4-o-carbonyl-protected thiosialoside donors in dichloromethane: facile and selective cleavage of the oxazolidinone ring.

Authors:  David Crich; Wenju Li
Journal:  J Org Chem       Date:  2007-03-06       Impact factor: 4.354

Review 8.  C-5 modifications in N-acetyl-neuraminic acid: scope and limitations.

Authors:  Cristina De Meo; Uvege Priyadarshani
Journal:  Carbohydr Res       Date:  2008-04-10       Impact factor: 2.104

9.  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

10.  Regioselective strategies mediated by lanthanide triflates for efficient assembly of oligomannans.

Authors:  K N Jayaprakash; Siddhartha Ray Chaudhuri; Changalvala V S R Murty; Bert Fraser-Reid
Journal:  J Org Chem       Date:  2007-06-27       Impact factor: 4.354
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  15 in total

1.  Influence of the O3 protecting group on stereoselectivity in the preparation of C-mannopyranosides with 4,6-O-benzylidene protected donors.

Authors:  David Crich; Indrajeet Sharma
Journal:  J Org Chem       Date:  2010-11-11       Impact factor: 4.354

2.  Stereoselective synthesis of alpha-keto-deoxy-D-glycero-D-galacto-nonulosonic acid glycosides by means of the 4,5-O-carbonate protecting group.

Authors:  David Crich; Chandrasekhar Navuluri
Journal:  Angew Chem Int Ed Engl       Date:  2010-04-12       Impact factor: 15.336

Review 3.  Advances in the biology and chemistry of sialic acids.

Authors:  Xi Chen; Ajit Varki
Journal:  ACS Chem Biol       Date:  2010-02-19       Impact factor: 5.100

4.  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

5.  Influence of protecting groups on the anomeric equilibrium; case of the 4,6-O-benzylidene acetal in the mannopyranose series.

Authors:  Indrajeet Sharma; Luis Bohé; David Crich
Journal:  Carbohydr Res       Date:  2012-06-07       Impact factor: 2.104

6.  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

7.  Dissecting the influence of oxazolidinones and cyclic carbonates in sialic acid chemistry.

Authors:  Pavan K Kancharla; Chandrasekhar Navuluri; David Crich
Journal:  Angew Chem Int Ed Engl       Date:  2012-09-13       Impact factor: 15.336

Review 8.  Recent progress in chemical and chemoenzymatic synthesis of carbohydrates.

Authors:  Saddam Muthana; Hongzhi Cao; Xi Chen
Journal:  Curr Opin Chem Biol       Date:  2009-10-14       Impact factor: 8.822

9.  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

10.  Parallel chemoenzymatic synthesis of sialosides containing a C5-diversified sialic acid.

Authors:  Hongzhi Cao; Saddam Muthana; Yanhong Li; Jiansong Cheng; Xi Chen
Journal:  Bioorg Med Chem Lett       Date:  2009-08-26       Impact factor: 2.823
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