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Synthesis of Carbohydrates and Carbohydrate Mimetics

Synthesis of Carbohydrates and Carbohydrate Mimetics


M. Jasiński*, G. Utecht, A. Fruziński, H.-U. Reißig
Three-Step Synthesis of 3-Aminoseptanoside Derivatives Using Lithiated Methoxyallene and δ-Siloxynitrones
Synthesis 2016, 48, 893 – 905.

J. Salta, J. Dernedde, H.-U. Reißig*
Synthesis of Multivalent Carbohydrate Mimetics with Aminopolyol End Groups and their Evaluation as L-Selectin Inhibitors
Beilstein J. Org. Chem. 2015, 11, 638 – 646.

J. Salta, H.-U. Reißig*
Synthesis of Divalent Carbohydrate Mimetics by Reductive Amination with Enantiopure 1,2-Oxazines as Precursors
Synthesis 2015, 47, 1893 – 1898.

M. Kandziora, E. Mucha, S. P. Zucker, H.-U.Reißig*
Syntheses of Mono- and Divalent C-Aminoglycosides Using 1,2-Oxazine Chemistry and Olefin Metathesis
Synlett 2015, 26, 367 – 374.

M. Kandziora, H.-U. Reißig*
Preparation of Multivalent Carbohydrate Mimetics Based on Enantiopure 1,2-Oxazines by Sonogashira Coupling and Subsequent Reductive Ring-Opening
Eur. J. Org. Chem. 2015, 370 – 377.

L. Bouché, M. Kandziora, H.-U. Reißig*
Synthesis of New Enantiopure Poly(hydroxy)aminooxepanes as Building Blocks for Multivalent Carbohydrate Mimetics
Beilstein J. Org. Chem. 2014, 10, 213 – 223.

M. Jasiński, Dieter Lentz, E. Moreno-Clavijo, H.-U. Reißig*
Application of L-Erythrose-Derived Nitrones in the Synthesis of Polyhydroxylated Compounds via 3,6-Dihydro-2H-1,2-oxazine Derivatives
Eur. J. Org. Chem. 2012, 3304 – 3316.

M. Jasiński, Dieter Lentz, H.-U. Reißig*
Carbohydrate-Auxiliary Assisted Preparation of Enantiopure 1,2-Oxazine Derivatives and Aminopolyols
Beilstein J. Org. Chem. 2012, 8, 662-674.

L. Bouché, H.-U. Reißig*
Synthesis of Novel Carbohydrate Mimetics via 1,2-Oxazines
Pure Appl. Chem. 2012, 84, 23 – 36.

M. Roskamp, S. Enders, F. Pfrengle, S. Yekta. V. Dekaris, J. Dernedde, H.-U. Reißig, S. Schlecht*
Multivalent Interaction and Selectivities in Selectin Binding of Functionalized Gold Colloids Decorated with Carbohydrate Mimetics
Org. Biomol. Chem. 2011, 9, 7448 – 7456.

V. Dekaris, R. Pulz, A. Al-Harrasi, D. Lentz, H.-U. Reißig*
Stereoselective Synthesis of Aza, Amino and Imion Sugar Derivatives by Hydroboration of 3,6-Dihydro-2H-1,2-oxazines as Key Reaction
Eur. J. Org. Chem. 2011, 3210 – 3219.

G. Semini, A. Hildmann, H.-U. Reißig, W. Reutter, K. Danker*
The Novel Synthetic Ether Lipid Inositol-C2-PAF Inhibits Phosphorylation of the Tyrosine Kinases Src and FAK Independent of Integrin Activation in Transformed Skin Cells
Biochemical Pharmacology 2011, 81, 985 – 995.

A. Al-Harrasi, L. Bouché, R. Zimmer, H.-U. Reißig*
β-Alkoxy-γ-amino Aldehydes by Internal Redox Ring Cleavages of Carbohydrate-Derived Enantiopure 1,2-Oxazines and Preparation of Heterocycles with Aminopolyol Side Chain
Synthesis 2011, 109 – 118.

F. Pfrengle, H.-U. Reißig*
Internally Protected Amino Sugar Equivalents from Enantiopure 1,2-Oxazines: Synthesis of Variably Configured Carbohydrates with C-Branched Amino Sugar Units
Chem. Eur. J. 2010, 16, 11915  –  11925.

F. Pfrengle, H.-U. Reißig*
Addition of Lithiated Enol Ethers to Nitrones and Subsequent Lewis Acid Induced Cyclizations to Enantiopure 3,6-Dihydro-2H-pyrans – an Approach to Carbohydrate Mimetics
Beilstein Journal of Organic Chemistry 2010, 6, No. 75.

F. Pfrengle, H.-U. Reißig*
Amino Sugars and their Mimetics via 1,2-Oxazines
Chem. Soc. Rev., 2010, 39, 549 – 557.

A. Al-Harrasi, S. Fischer, R. Zimmer, H.-U. Reißig*
Ring Enlargement of Carbohydrate-Derived 1,2-Oxazines to Enantiopure 5-Bromo-1,2-oxazepines and Subsequent Palladium-Catalyzed Reactions
Synthesis 2010, 304 – 314.

V. Dekaris, B. Bressel, H.-U. Reißig*
Acid Mediated Transformations of Enantiopure 3,6-Dihydro-2H-1,2-oxazines into Functionalized Aminotetrahydrofuran Derivatives
Synlett 2010, 47 – 50.

V. Dekaris, H.-U. Reißig*
Stereocontrolled Syntheses of Enantiopure Polyhydroxylated Azetidines via 1,2-Oxazines
Synlett 2010, 42 – 46.

F. Pfrengle, D. Lentz, H.-U. Reißig*
A New Ring Closure Approach to Enantiopure 3,6-Dihydro-2H-pyrans: Stereodivergent Access to Carbohydrate Mimetics
Org. Lett. 2009, 11, 5534 – 5537.

A. Al-Harrasi, F. Pfrengle, V. Prisyazhnyuk, S. Yekta, P. Koóš, H.-U. Reißig*
Enantiopure Aminopyrans by a Lewis Acid Promoted Rearrangement of 1,2-Oxazines: Versatile Building Blocks for Oligosaccharide and Sugar Amino Acid Mimetics
Chem. Eur. J. 2009, 15, 11632  –  11642

M. Brasholz, H.-U. Reißig*
Alkoxyallene-Based De Novo Synthesis of Rare Deoxy Sugars: New Routes to L-Cymarose, L-Sarmentose, L-Diginose and L-Oleandrose
Eur. J. Org. Chem. 2009, 3595– 3604.

•  F. Pfrengle, D. Lentz, H.-U. Reißig*
Stereodivergente De-novo-Synthese verzweigter Aminozucker durch Lewis-Säure-induzierte Umlagerung von 1,2-Oxazinen
Angew. Chem. 2009, 121, 3211 - 3215.

  F. Pfrengle, D. Lentz, H.-U. Reißig*
Stereodivergent De novo Synthesis of Branched Amino Sugars by Lewis Acid promoted Rearrangement of 1,2-Oxazines
Angew. Chem. Int. Ed. 2009, 48, 3165 - 3169.

•  B. Bressel, H.-U. Reißig*
A New Approach to Neuraminic Acid Analogues via 1,2-Oxazines
Org. Lett. 2009, 11, 527 – 530.

•  F. Pfrengle, A. Al-Harrasi, I. Brüdgam, H.-U. Reißig*
Unusual Enantiopure Heterocyclic Skeletons via Lewis Acid Promoted Rearrangements of 1,3-Dioxolanyl-Substituted 1,2-Oxazines
Eur. J. Org. Chem. 2009, 282 – 291.

E. Hýrošovà, L. Fišera,* M. Medvecký, H.-U. Reißig, A. Al-Harrasi, M. Koòš
From sugars to modified nucleosides
ARKIVOC 2009 (ix), 122 - 142.

B. Bressel, B. Egart, A. Al-Harrasi, R. Pulz, H.-U. Reißig,* I. Brüdgam
Acid-Induced and Reductive Transformations of Enantiopure 3,6-Dihydro-2H-1,2-oxazines – Synthesis of Dideoxyamino Carbohydrate Derivatives
Eur. J. Org. Chem. 2008, 467 – 474.

S. Yekta, V. Prisyazhnyuk, H.-U. Reißig*
Simple Modifications of Enantiopure 1,2-Oxazines Leading to Building Blocks for Carbohydrate and Peptide Mimetics
Synlett 2007, 2069 – 2072.

M. Brasholz, H.-U. Reißig*
Oxidative Spaltung von 3-Alkoxy-2,5-dihydrofuranen und ihre Anwendung in der De-novo-Synthese seltener Monosaccharide am Beispiel von L-Cymarose
Angew. Chem. 2007, 119, 1659 – 1662; Angew. Chem. Int. Ed. 2007, 46, 1634  –  1637.

A. Al-Harrasi, I. Brüdgam, H. Hartl, H.-U. Reißig*
Crystal structure of 1R,5S,8R,9S-8-azidomethyl-2-benzyl-
6,6-dimethyl-3,7-dioxa-2-aza-bicyclo[3.3.1]nonan-9-0l, C16H22N4O3

Z. Kristallogr. NCS 2005, 220, 599 - 600.

A. Al-Harrasi, I. Brüdgam, H. Hartl, H.-U. Reißig*
Crystal structure of 3S,4S,5R,6S,7R-5-amino-6-(tert-butyldimethylsiloxy)-
7(tert-butyldimethylsiloxymethyl)-3-hydroxymethyl-2,2-dimethyloxepan-4-ol, C22H49NO5Si2
Z. Kristallogr. NCS 2006, 221, 131 – 132.

A. Al-Harrasi, H.-U. Reißig*
Enantiomerenreiner Kohlenhydratmimetika durch Lewis-Säure-induzierte Umlagerung von 1,3-dioxolanyl-substitutierten 3,6-Dihydro-2H-1,2-oxazinen
Angew. Chem. 2005, 117, 6383 - 6387.

A. Al-Harrasi, H.-U. Reißig*
Synthesis of Enantiopure Carbohydrate Mimetics by Lewis Acid Catalyzed Rearrangement of 1,3-Dioxolanyl-Substituted 1,2-Oxazines
Angew. Chem. Int. Ed. 2005, 44, 6227  –  6231.

A. Al-Harrasi, H.-U. Reißig*
Synthesis of Enantiopure Functionalized β-Alkoxy γ-Amino Aldehydes by a New Internal Redox Ring Cleavage of Carbohydrate Derived 1,2-Oxazines
Synlett 2005, 1152 – 1154.

R. Pulz, A. Al-Harrasi, H.-U. Reißig*
Acid Promoted Syntheses of New Enantiopure Amino Sugar Derivatives from 3,6-Dihydro-2H-1,2-oxazines
Synlett 2002, 817 – 819.