Abstract
Recent advances in stereocontrolled Wittig olefination of sugars with stabilized and semi-stabilized phosphoranes are reviewed. Transformations of free and protected sugars for chain elongation at both reducing and terminal ends, and branched chain construction at the carbon atoms 2, 3 and 5 demonstrate the usefulness of this reaction in the preparation of a number of biologically active molecules and their precursors, starting from readily available sugars. Higher sugars, bicyclic structures, and C-C linked oligosaccharides lie amongst the diversity of compounds shown in this review that are synthesized by this reaction, easily carried out and efficient in terms of reaction yield and stereoselectivity, depending on reagents and reaction conditions.
The analogy of aza-Wittig reaction, based on reaction of N-alkyl-triphenyl-λ5-phosphanimines with aldehydes or ketones, encouraged us to consider its contribution for the synthesis of N-linked sugars and imino sugars, which have biological and - some of them - industrial application as inhibitors of glycoprocessing enzymes. The use of this reaction for the preparation of pseudonucleosides with the N-linked appendages, N-linked and thiazolidinone-linked saccharides, and a diversity of imino sugars will be highlighted and the reaction stereocontrol discussed.
Keywords: Aza-Wittig reaction, stereocontrol, Wittig olefination.
Current Organic Chemistry
Title:Revisiting Wittig Olefination and Aza-Wittig Reaction for Carbohydrate Transformations and Stereocontrol in Sugar Chemistry
Volume: 18 Issue: 13
Author(s): Vasco Cachatra and Amelia P. Rauter
Affiliation:
Keywords: Aza-Wittig reaction, stereocontrol, Wittig olefination.
Abstract: Recent advances in stereocontrolled Wittig olefination of sugars with stabilized and semi-stabilized phosphoranes are reviewed. Transformations of free and protected sugars for chain elongation at both reducing and terminal ends, and branched chain construction at the carbon atoms 2, 3 and 5 demonstrate the usefulness of this reaction in the preparation of a number of biologically active molecules and their precursors, starting from readily available sugars. Higher sugars, bicyclic structures, and C-C linked oligosaccharides lie amongst the diversity of compounds shown in this review that are synthesized by this reaction, easily carried out and efficient in terms of reaction yield and stereoselectivity, depending on reagents and reaction conditions.
The analogy of aza-Wittig reaction, based on reaction of N-alkyl-triphenyl-λ5-phosphanimines with aldehydes or ketones, encouraged us to consider its contribution for the synthesis of N-linked sugars and imino sugars, which have biological and - some of them - industrial application as inhibitors of glycoprocessing enzymes. The use of this reaction for the preparation of pseudonucleosides with the N-linked appendages, N-linked and thiazolidinone-linked saccharides, and a diversity of imino sugars will be highlighted and the reaction stereocontrol discussed.
Export Options
About this article
Cite this article as:
Cachatra Vasco and Rauter P. Amelia, Revisiting Wittig Olefination and Aza-Wittig Reaction for Carbohydrate Transformations and Stereocontrol in Sugar Chemistry, Current Organic Chemistry 2014; 18 (13) . https://dx.doi.org/10.2174/1385272819666140527230833
DOI https://dx.doi.org/10.2174/1385272819666140527230833 |
Print ISSN 1385-2728 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-5348 |
Call for Papers in Thematic Issues
Advances of Heterocyclic Chemistry with Pesticide Activity
Global food safety and security will continue to be a global concern for the next 50 years and beyond. Plant diseases have had a significant impact on food safety and security throughout the entire food chain, from primary production to consumption. While conventional chemical pesticides have been traditionally used for ...read more
Calculation design of covalent/metal organic framework based catalysts
This research area combines theoretical computation and screening with machine learning for the design of covalent/metal organic framework-based catalysts, bridging the disciplines of organic chemistry, physical chemistry, computational chemistry, materials science, and machine learning. It covers several critical aspects: designing and synthesizing organic catalysts for improved performance, applying computational methods ...read more
Carbohydrates conversion in biofuels and bioproducts
Biomass pretreatment, hydrolysis, and saccharification of carbohydrates, and sugars bioconversion in biofuels and bioproducts within a biorefinery framework. Carbohydrates derived from woody biomass, agricultural wastes, algae, sewage sludge, or any other lignocellulosic feedstock are included in this issue. Simulation, techno-economic analysis, and life cycle analysis of a biorefinery process are ...read more
Catalytic C-H bond activation as a tool for functionalization of heterocycles
The major topic is the functionalization of heterocycles through catalyzed C-H bond activation. The strategies based on C-H activation not only provide straightforward formation of C-C or C-X bonds but, more importantly, allow for the avoidance of pre-functionalization of one or two of the cross-coupling partners. The beneficial impact of ...read more
Related Journals
- Author Guidelines
- Graphical Abstracts
- Fabricating and Stating False Information
- Research Misconduct
- Post Publication Discussions and Corrections
- Publishing Ethics and Rectitude
- Increase Visibility of Your Article
- Archiving Policies
- Peer Review Workflow
- Order Your Article Before Print
- Promote Your Article
- Manuscript Transfer Facility
- Editorial Policies
- Allegations from Whistleblowers
- Announcements
Related Articles
-
Aligning Animal Models of Clinical Germinal Matrix Hemorrhage, From Basic Correlation to Therapeutic Approach
Current Drug Targets Compartmentalized and Internally Structured Particles for Drug Delivery - A Review
Current Pharmaceutical Design Is it Necessary to Calculate Young’s Modulus in AFM Nanoindentation Experiments Regarding Biological Samples?
Micro and Nanosystems Multi-Classifier Based on Hard Instances- New Method for Prediction of Human Immunodeficiency Virus Drug Resistance
Current Topics in Medicinal Chemistry Voltage-Gated Sodium Channel Blockers for the Treatment of Chronic Pain
Current Topics in Medicinal Chemistry Modulation of the Endocannabinoid System by Lipid Rafts
Current Medicinal Chemistry Immunogenicity Assessment of Therapeutic Proteins and Peptides
Current Pharmaceutical Biotechnology The Changing Role of Radiation in the Post-TME ERA of Rectal Cancer
Current Cancer Therapy Reviews Determination of Human Serum α1-Acid Glycoprotein and Albumin Binding of Various Marketed and Preclinical Kinase Inhibitors
Current Medicinal Chemistry Resveratrol in Medicinal Chemistry: A Critical Review of its Pharmacokinetics, Drug-Delivery, and Membrane Interactions
Current Medicinal Chemistry Immunomodulatory Effects of Soybeans and Processed Soy Food Compounds
Recent Patents on Food, Nutrition & Agriculture Non-Analgesic Effects of Opioids: The Interaction of Opioids with Bone and Joints
Current Pharmaceutical Design Evaluation of Drug Transporter Interactions in Drug Discovery and Development
Combinatorial Chemistry & High Throughput Screening Multi-target Pharmacological Effects of Platycodin D
Mini-Reviews in Organic Chemistry Cordycepin in Anticancer Research: Molecular Mechanism of Therapeutic Effects
Current Medicinal Chemistry A Compendium of Volatile Organic Compounds (VOCs) Released By Human Cell Lines
Current Medicinal Chemistry Autoimmune Diseases in Gastroenterology
Current Pharmaceutical Design Structure and Ligand Based Drug Design Strategies in the Development of Novel 5- LOX Inhibitors
Current Medicinal Chemistry 5-Aryl-1,3,4-Thiadiazole-Based Hydroxamic Acids as Histone Deacetylase Inhibitors and Antitumor Agents: Synthesis, Bioevaluation and Docking Study
Medicinal Chemistry Sodium Carbonate Sesquiperhydrate (2Na2CO3-3H2O2) Catalysed One-pot Synthesis of Biologically Dynamic Novel Substituted Spirooxirane Dicarboxamides
Current Catalysis