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9pe Carbohydrate-Based Lactones:Synthesis and Applications Nuno M.Xavier,Amelia P.Rauter,and Yves Queneau Abstract The synthesis and uses of different kinds of carbohydrate-based lactones are described.This group of compounds includes aldonolactones,other related systems..The latter。 an arise from uronic acids Keywords Aldonolactones,Bicyclic lactones,Gluconolactone,Sugar lactones, Synthons,Uronic acids Contents tion 2.1 General Aspects. 2 N.M.Xay o de Quimicae bioguimi ade de Ciencias da Universidade de Lisbos.Ed..Campo Grande.1749-016.Lisboa.Portugal Laboratoire de Chimie Organique,INSA Lyon,Batiment J.Verne,20 av A.Einstein,69621. ranc Riochimie moleculaires e mokeculaires,UMR 5246.Universite Lyon 1 Universite de Lyon,INSA-Lyon,CNRS.CPE-Lyon,Villeurbanne,France AP.Rauter(☒ Y.Queneau(☒ Chimie Organique,INSA Lyon,Batiment J.Verne.20 avA.Einstein,69621 Institut de Chimie et Biochimie Moleculaireset Supramoculaires,UMR 5246.Universite Lyon 1 Bitiment CPE.43 bd du 11 novembre 1918.6922,Villeurbanne.France onCNRS.CPE-Lyon,Villeurbanne.France
Top Curr Chem (2010) 295: 19–62 DOI: 10.1007/128_2010_61 # Springer‐Verlag Berlin Heidelberg 2010 Published online: 1 February 2010 Carbohydrate-Based Lactones: Synthesis and Applications Nuno M. Xavier, Ame´lia P. Rauter, and Yves Queneau Abstract The synthesis and uses of different kinds of carbohydrate-based lactones are described. This group of compounds includes aldonolactones, other related monocyclic lactones and bicyclic systems. The latter can arise from uronic acids, carboxymethyl ethers or glycosides, or from C-branched sugars. Keywords Aldonolactones, Bicyclic lactones, Gluconolactone, Sugar lactones, Synthons, Uronic acids Contents 1 Introduction . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 21 2 Aldonolactone Synthesis . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 21 2.1 General Aspects . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 21 N.M. Xavier Centro de Quı´mica e Bioquı´mica, Departamento de Quı´mica e Bioquı´mica, Faculdade de Cieˆncias da Universidade de Lisboa, Ed. C8, 5 Piso, Campo Grande, 1749-016, Lisboa, Portugal Laboratoire de Chimie Organique, INSA Lyon, Baˆtiment J. Verne, 20 av A. Einstein, 69621, Villeurbanne, France Institut de Chimie et Biochimie Mole´culaires et Supramole´culaires, UMR 5246, Universite´ Lyon 1, Baˆtiment CPE, 43 bd du 11 novembre 1918, 69622, Villeurbanne, France Universite´ de Lyon, INSA-Lyon, CNRS, CPE-Lyon, Villeurbanne, France A.P. Rauter (*) Centro de Quı´mica e Bioquı´mica, Departamento de Quı´mica e Bioquı´mica, Faculdade de Cieˆncias da Universidade de Lisboa, Ed. C8, 5 Piso, Campo Grande, 1749-016, Lisboa, Portugal Y. Queneau (*) Laboratoire de Chimie Organique, INSA Lyon, Baˆtiment J. Verne, 20 av A. Einstein, 69621, Villeurbanne, France Institut de Chimie et Biochimie Mole´culaires et Supramole´culaires, UMR 5246, Universite´ Lyon 1, Baˆtiment CPE, 43 bd du 11 novembre 1918, 69622, Villeurbanne, France Universite´ de Lyon, INSA-Lyon, CNRS, CPE-Lyon, Villeurbanne, France e-mail: yves.queneau@insa‐lyon.fr
20 N.M.Xavier et al 2.2 23 24 Aldono-l 4-I actone Aldonolactones as Useful Chirons Synt 3 Synthesis of L-Aldoses 3.4 Synthesis of Iminoalditols and Analogs 36 Synthesis Thio Products 34 3.7 ,B-Unsaturated Aldonolactones 4 ed Lactones and Glycosides 5 4 3 Fused C.Branched I act 5 Conclusion.. References Abbreviations AAPDH 2.2'-Azobis(2-amidinopropan)dihydrochloride AD Asymmetric dihydroxylation Albn 2.2'-Azobisisobutyronitrile M Critical micellar concentration M xymethyl gly CMGL Carboxymethy glyc CS. Camphorsulfonic acid CQide2.0-lhaconc DCC Dicyclohexylcarbodiimide DEAD Diethyl azodicarboxylate DIBAL-H Diisobutylaluminum hydride DMAP DMI -um 1-Deoxymannoiirim DNJ GABA roperoxybenzoic acid esyl(me sulfonyl) Microwave irradiation NBS W-Bromosuccinimide NeuAc N-Acetyl neuraminic acid NIS N-lodosuccinimide NMO N-Methylmorpholine N-oxide Oct Octoate (2-ethylhexanoate) PCO Pyridinium chlo rochrom loyl PMPOH p-Methoxyphenol
2.2 Glucono-1,5-Lactone . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 22 2.3 Other Aldono-1,5-Lactones . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 23 2.4 Aldono-1,4-Lactones . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 23 3 Aldonolactones as Useful Chirons . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 26 3.1 Synthesis of Surfactants and Polymers . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 26 3.2 Synthesis of C-Glycosyl Compounds . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 33 3.3 Synthesis of L-Aldoses . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 35 3.4 Synthesis of Iminoalditols and Analogs . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 36 3.5 Synthesis of Thiosugars . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 39 3.6 Synthesis of Bioactive Natural Products . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 40 3.7 a,b-Unsaturated Aldonolactones . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 41 4 Bicyclic Carbohydrate-Based Lactones . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 42 4.1 Uronic Acid Derived Lactones . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 42 4.2 Lactonized Carboxyalkyl Ethers and Glycosides . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 45 4.3 Fused C-Branched Lactones . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 50 5 Conclusion . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 56 References . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 56 Abbreviations AAPDH 2,2’-Azobis(2-amidinopropan) dihydrochloride AD Asymmetric dihydroxylation AIBN 2,2’-Azobisisobutyronitrile CMC Critical micellar concentration CMG Carboxymethyl glycoside CMGL Carboxymethyl glycoside 2-O-lactones CSA Camphorsulfonic acid DCC Dicyclohexylcarbodiimide DEAD Diethyl azodicarboxylate DIBAL-H Diisobutylaluminum hydride DMAP 4-(Dimethylamino)pyridine DMJ 1-Deoxymannojirimycin DNJ Deoxynojirimycin GABA g-Aminobutyric acid mCPBA m-Chloroperoxybenzoic acid Ms Mesyl (methanesulfonyl) MW Microwave irradiation NBS N-Bromosuccinimide NeuAc N-Acetyl neuraminic acid NIS N-Iodosuccinimide NMO N-Methylmorpholine N-oxide Oct Octoate (2-ethylhexanoate) PCC Pyridinium chlorochromate PDC Pyridinium dichromate Piv Pivaloyl PMPOH p-Methoxyphenol 20 N.M. Xavier et al