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. [10.1002/(SICI)1099-0690(199912)1999:12<3437::AID-EJOC3437>3.0.CO;2-0]
Conversion of lactose into mimics of N-acetyllactosamine
L. LayPrimo
;
1999
Abstract
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.
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