A novel general method for 2-aminoglycal synthesis

✍ Scribed by Fernando Iglesia-Guerra; José I. Candela; José L. Espartero; José M. Vega-Pérez

• Publisher: Elsevier Science
• Year: 1994
• Tongue: French
• Weight: 287 KB
• Volume: 35
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)73312-0

✦ Synopsis

The fiit general metkod ~~~-~~ bigly is report&. We desailn? the symtwcs of 2-[~~-acyl-~-~yl~ino~ and 2-[(N~N-dia~kyl)amino]-l.S-an~ydro-Q~~O-benzy~i~~-2-derrxy-cry-1~-3-ulos*r by oxidatioa of glycosida derivatives of N,hMstitatcd-Z-aminosugars using two oxidant systems. Rcactims proceed with good yields. Glycal derivatives have piayed a mjor mle in c~hy~~ chemistry as precu~or substances in the synthesis of glycosidest, thioglycosides? oligosaccharides~, 2-deoxymtcleoside~ and C-giycosidess, as well as in that of C& &unWurated iactones6. There are many works on glycal and 2-hydroxyglycal7 p~paration, but many fewer on the synthesis of hex-l-en-3-ulose derivatives 8. moreover there are scarce anwedents for the preparation of Zaminoglycal derivatives (1) and (2). Such antecedents for the preparation of compounds 1 and 2 refer to non-general procedures of certain substances with acetyl or methyi group on the nitrogens, or of other substances obtained as unwon byproducts in glycosidationt@ or &-methyiation of ketone@. In view of the scarcity of the antecedents found and due to our interest in 2-aminoglycal derivatives, in this paper we describe for the first time a good general method for the synthqis of 2-[(N-acyl-N-~l)~nol-l,5-anh~,~O-bcn~~~~2~xy~-cryrluo-hex-l~-3-~s. This general method consists of the oxidation of g&co&k derivatives of ~,~-substi~ted-2aminosugats. Here, WC dcscribc the synthesis of substances 3-8 from 2-~~su~ (9-19)t2 using two 5031