Borbas, Aniko et al. published their research in Tetrahedron in 2002 |CAS: 130539-43-4

The Article related to naphthyl methylene acetal glycoside preparation, naphthylmethyl ether glycoside regioselective preparation, me acetyl naphthylmethylene galactopyranoside preparation crystal mol structure and other aspects.Synthetic Route of 130539-43-4

On July 8, 2002, Borbas, Aniko; Szabo, Zoltan B.; Szilagyi, Laszlo; Benyei, Attila; Liptak, Andras published an article.Synthetic Route of 130539-43-4 The title of the article was Dioxane-type (2-naphthyl)methylene acetals of glycosides and their hydrogenolytic transformation into 6-O- and 4-O-(2-naphthyl)methyl (NAP) ethers. And the article contained the following:

α-, β-D-Gluco-, galacto-, 2-deoxy-2-phthalimido-β-D-glucopyranosides with different aglycons (Me, allyl, p-methoxyphenyl, thioethyl) reacted with 2-naphthaldehyde di-Me acetal to give rise to 4,6-O-(2-naphthyl)methylene acetals. The acetals were converted into fully protected compounds bearing benzoyl, benzyl, allyl, p-methoxybenzyl groups. The fully alkylated dioxane-type acetals were hydrogenolyzed with AlH3 (3LiAlH4-AlCl3) reagent to furnish 4-O-NAP/6-OH derivatives All acetals were treated with BH3·Me3N-AlCl3 in THF and a reverse regioselectivity was observed, producing 6-O-NAP/4-OH derivatives Similar regioselectivity was also observed by using NaCNBH3-HCl reagent. In all reactions very mild reaction conditions were required, regioselectivity was better than 93:7, and the isolated yields were between 83-92%. All compounds were characterized by 1H and 13C NMR spectra. Solid-state and solution conformation of Me 2,3-di-O-acetyl-4,6-O-(2-naphthyl)methylene-α-D-galactopyranoside were elucidated by X-ray and NMR measurements. The experimental process involved the reaction of Ethyl 2-deoxy-2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-1-thio-beta-D-glucopyranoside(cas: 130539-43-4).Synthetic Route of 130539-43-4

The Article related to naphthyl methylene acetal glycoside preparation, naphthylmethyl ether glycoside regioselective preparation, me acetyl naphthylmethylene galactopyranoside preparation crystal mol structure and other aspects.Synthetic Route of 130539-43-4

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles