Carbohydrates in Sustainable Development II pp 19-62

Part of the Topics in Current Chemistry book series (TOPCURRCHEM, volume 295) | Cite as

Carbohydrate-Based Lactones: Synthesis and Applications

  • Nuno M. Xavier
  • Amélia P. Rauter
  • Yves Queneau
Chapter

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 

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

γ-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

PPL

Porcine pancreatic lipase

Py

Pyridine

ROP

Ring-opening polymerization

TBAF

Tetrabutylammonium fluoride

TBDMS

tert-Butyldimethylsilyl

Tf

Trifluoromethanesulfonyl (triflyl)

TFA

Trifluoroacetic acid

TFAA

Trifluoroacetic anhydride

TMEDA

N,N,N',N'-Tetramethyl-1,2-ethylenediamine

TMS

Trimethylsilyl

TPAP

Tetrapropylammonium perruthenate

Ts

Tosyl, 4-toluenesulfonyl

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Copyright information

© Springer 2010

Authors and Affiliations

  • Nuno M. Xavier
    • 1
    • 2
    • 3
    • 4
  • Amélia P. Rauter
    • 1
  • Yves Queneau
    • 2
    • 3
    • 4
  1. 1.Centro de Química e Bioquímica, Departamento de Química e BioquímicaFaculdade de Ciências da Universidade de LisboaLisboaPortugal
  2. 2.Laboratoire de Chimie OrganiqueINSA LyonVilleurbanneFrance
  3. 3.Institut de Chimie et Biochimie Moléculaires et SupramoléculairesUMR 5246, Université Lyon 1, Bâtiment CPEVilleurbanneFrance
  4. 4.Université de Lyon, INSA-Lyon, CNRS, CPE-LyonVilleurbanneFrance

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