Conversion of Lactose into Mimics of N-Acetyllactosamine

✍ Scribed by Luigi Lay; Laura Cipolla; Barbara La Ferla; Francesco Peri; Francesco Nicotra

• Publisher: John Wiley and Sons
• Year: 1999
• Tongue: English
• Weight: 275 KB
• Volume: 1999
• Category: Article
• ISSN: 1434-193X
• DOI: 10.1002/(sici)1099-0690(199912)1999:12<3437::aid-ejoc3437>3.0.co;2-0

✦ Synopsis

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