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Titolo:
Directed and efficient syntheses of beta(1 -> 4)-linked galacto-oligosaccharides
Autore:
Lichtenthaler, FW; Oberthur, M; Peters, S;
Indirizzi:
Tech Univ Darmstadt, Inst Organ Chem, D-64287 Darmstadt, Germany Tech UnivDarmstadt Darmstadt Germany D-64287 D-64287 Darmstadt, Germany
Titolo Testata:
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
fascicolo: 20, , anno: 2001,
pagine: 3849 - 3869
SICI:
1434-193X(200110):20<3849:DAESOB>2.0.ZU;2-X
Fonte:
ISI
Lingua:
ENG
Soggetto:
CELL-SURFACE GLYCANS; CHLOROTRIMETHYLSILANE SODIUM-IODIDE; METHYL BETA-GLYCOSIDES; BLOOD-GROUP SUBSTANCES; L-FUCOPYRANOSYL GROUPS; ONE-ELECTRON-TRANSFER; ANTIGENIC DETERMINANT; CARBOHYDRATE MOIETY; HOMOGENEOUS REAGENT; TRYPANOSOMA-BRUCEI;
Keywords:
carbohydrates; glycosides; glycosylations; oligosaccharides; thiogalatosides;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Physical, Chemical & Earth Sciences
Citazioni:
96
Recensione:
Indirizzi per estratti:
Indirizzo: Lichtenthaler, FW Tech Univ Darmstadt, Inst Organ Chem, Petersenstr 22, D-64287 Darmstadt, Germany Tech Univ Darmstadt Petersenstr 22 Darmstadt Germany D-64287
Citazione:
F.W. Lichtenthaler et al., "Directed and efficient syntheses of beta(1 -> 4)-linked galacto-oligosaccharides", EUR J ORG C, (20), 2001, pp. 3849-3869

Abstract

Straightforward, preparatively efficient procedures are described for the construction of beta (1 -->4)-intergalactosidic linkages up to the hexasaccharide level. Key elements were the use of phenylthio and/or phenyl sulfoxide functionalities for glycosylations and a judiciously designed blocking group pattern for donor and acceptor alike: pivaloyl protection at O-2 for securing beta -selectivity, sterically undemanding allyl or benzyl groups atO-3 and O-6 to minimise the steric bulk around the unreactive galactosyl-4-OH, the p-methoxy-phenyl moiety, readily replaceable by SPh, as an intermediate anomeric substituent, and an acetyl group for temporary. protection of the terminal Gal-4-OH. This strategy lends itself to iterative block synthesis and interchange of donors and acceptors, thereby demonstrating the broad scope and generality of the overall approach. Although predicted by molecular modelling, inclinations towards starch-like coiling could not so farbe verified in any of the galacto-tetra-, -penta-, or -hexaoses or their p-methoxyphenyl glycosides.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 29/03/20 alle ore 09:27:16