The alpha-C-Glycoside of N-acetyllactosamine 8 was synthesised from lactose by acetylation, conversion into the allyl alpha-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 beta-C-glycoside of N-acetyllactosamine 11.
Conversion of lactose into mimics of N-acetyllactosamine / L. Lay, L. Cipolla, B. La Ferla, F. Peri, F. Nicotra. - In: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. - ISSN 1434-193X. - 1999:12(1999), pp. 3437-3440.
Titolo: | Conversion of lactose into mimics of N-acetyllactosamine |
Autori: | LAY, LUIGI (Primo) |
Parole Chiave: | Amino sugars; Carbohydrates; Glycomimetics; Glycosides; Lactosamine |
Settore Scientifico Disciplinare: | Settore CHIM/06 - Chimica Organica |
Data di pubblicazione: | 1999 |
Rivista: | |
Tipologia: | Article (author) |
Digital Object Identifier (DOI): | http://dx.doi.org/10.1002/(SICI)1099-0690(199912)1999:12<3437::AID-EJOC3437>3.0.CO;2-0 |
Appare nelle tipologie: | 01 - Articolo su periodico |