The α-C-Glycoside of N-acetyllactosamine 8 was synthesised from lactose by acetylation, conversion into the allyl α-C-glycoside 4, exchanging the protecting groups for benzyl ethers, selective deprotection at the gluco-C-2 by iodocyclisation-reductive elimination, and conversion of the free hydroxyl group into an acetamido group by oxidation, oximation, stereoselective reduction and acetylation. Isomerization of the C-glycosidic appendage by conversion into a 2-oxypropyl group and treatment with base gave, after acetylation, the β-C-glycoside of N-acetyllactosamine 11.

Lay, L., Cipolla, L., LA FERLA, B., Peri, F., & Nicotra, F. (1999). Conversion of Lactose into mimics of N-acetyllactosaminE. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY(12), 3437-3440.

Conversion of Lactose into mimics of N-acetyllactosaminE

CIPOLLA, LAURA FRANCESCA;LA FERLA, BARBARA;PERI, FRANCESCO;NICOTRA, FRANCESCO
1999

Abstract

The α-C-Glycoside of N-acetyllactosamine 8 was synthesised from lactose by acetylation, conversion into the allyl α-C-glycoside 4, exchanging the protecting groups for benzyl ethers, selective deprotection at the gluco-C-2 by iodocyclisation-reductive elimination, and conversion of the free hydroxyl group into an acetamido group by oxidation, oximation, stereoselective reduction and acetylation. Isomerization of the C-glycosidic appendage by conversion into a 2-oxypropyl group and treatment with base gave, after acetylation, the β-C-glycoside of N-acetyllactosamine 11.
Articolo in rivista - Articolo scientifico
Scientifica
Lactose, carbohydrates, glycomimetics
English
Lay, L., Cipolla, L., LA FERLA, B., Peri, F., & Nicotra, F. (1999). Conversion of Lactose into mimics of N-acetyllactosaminE. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY(12), 3437-3440.
Lay, L; Cipolla, L; LA FERLA, B; Peri, F; Nicotra, F
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/10281/16629
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