Organocatalytic synthesis of carbohydrates
- PMID: 21796310
- DOI: 10.1039/c1cs15144d
Organocatalytic synthesis of carbohydrates
Abstract
The key role of carbohydrates in biological processes and their visible existence in our everyday life have stimulated the interest of leading research groups on the smart and simple synthesis of common and rare sugar molecules. Now, more than 120 years after Fischer's first synthesis of (D)-glucose (1890), we are witnessing important development in this field of total synthesis. Using modern methods of direct activation of carbonyl compounds chemists can prepare sugars in an elegant and efficient way similar to that of Nature. This tutorial review presents recent impressive progress in the area of de novo synthesis of carbohydrates by using organocatalytic direct aldol reaction as a key step.
Similar articles
-
Synthesis of octitols and the respective amino-derivatives from 'organo-aldols'.Carbohydr Res. 2015 Feb 11;403:98-103. doi: 10.1016/j.carres.2014.07.010. Epub 2014 Jul 27. Carbohydr Res. 2015. PMID: 25130931
-
Total syntheses of carbohydrates: organocatalyzed aldol additions of dihydroxyacetone.Chemistry. 2008;14(1):40-8. doi: 10.1002/chem.200701334. Chemistry. 2008. PMID: 17973286
-
Synthesis of carbohydrates in a continuous flow reactor by immobilized phosphatase and aldolase.ChemSusChem. 2012 Dec;5(12):2348-53. doi: 10.1002/cssc.201200468. Epub 2012 Nov 13. ChemSusChem. 2012. PMID: 23150241
-
[Synthesis of carbohydrate related compounds by using aldolase catalyzed reaction].Yakugaku Zasshi. 2000 Jan;120(1):42-53. doi: 10.1248/yakushi1947.120.1_42. Yakugaku Zasshi. 2000. PMID: 10655781 Review. Japanese.
-
'Five at one stroke': proline and small peptides in the stereoselective de novo synthesis and enantiotopic functionalization of carbohydrates.Chem Biodivers. 2005 Jul;2(7):825-36. doi: 10.1002/cbdv.200590061. Chem Biodivers. 2005. PMID: 17193175 Review.
Cited by
-
Organocatalytic Synthesis of Higher-Carbon Sugars: Efficient Protocol for the Synthesis of Natural Sedoheptulose and d-Glycero-l-galacto-oct-2-ulose.ChemistryOpen. 2015 Jun 26;4(6):717-21. doi: 10.1002/open.201500099. eCollection 2015 Dec. ChemistryOpen. 2015. PMID: 27308197 Free PMC article.
-
Novel Brønsted Acid Catalyzed C-C Bond Activation and α-Alkylation of Ketones.Molecules. 2024 Sep 9;29(17):4266. doi: 10.3390/molecules29174266. Molecules. 2024. PMID: 39275113 Free PMC article.
-
Diversity-oriented synthesis of glycomimetics.Commun Chem. 2021 Jun 24;4(1):96. doi: 10.1038/s42004-021-00520-3. Commun Chem. 2021. PMID: 36697548 Free PMC article.
-
Saccharide success: exploring the role of d-fructose-based thioureas as organocatalysts for the enantioselective Friedel-Crafts alkylation reaction.RSC Adv. 2025 Mar 18;15(11):8335-8345. doi: 10.1039/d5ra00456j. eCollection 2025 Mar 17. RSC Adv. 2025. PMID: 40103969 Free PMC article.
-
On the Origin of Sugar Handedness: Facts, Hypotheses and Missing Links-A Review.Orig Life Evol Biosph. 2022 Sep;52(1-3):21-56. doi: 10.1007/s11084-022-09624-9. Epub 2022 Jul 7. Orig Life Evol Biosph. 2022. PMID: 35796896 Review.
Publication types
MeSH terms
Substances
LinkOut - more resources
Full Text Sources