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Isothiocyanates and cyclic thiocarbamates of α, α′-trehalose, sucrose, and cyclomaltooligosaccharides

✍ Scribed by JoséManuel García Fernández; Carmen Ortiz Mellet; JoséLuis Jiménez Blanco; José Fuentes Mota; Andrée Gadelle; Annie Coste-Sarguet; Jacques Defaye

Publisher
Elsevier Science
Year
1995
Tongue
English
Weight
844 KB
Volume
268
Category
Article
ISSN
0008-6215

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✦ Synopsis

6,6'-Dideoxy-6,6'-diisothiocyanato-a,a'-trehalose (4), 6-deoxy-6-isothiocyanato-a-D-fructofuranose fl-D-fructopyranose 1,2' : 2,1 '-dianhydride (11), 6,6'-dideoxy-6,6'-diisothiocyanatosucrose (16), and per(6-deoxy-6-isothiocyanato)-cyclomaltohexaose (23), -cyclomaltoheptaose (27), and -cyclomaltooctaose (31) have been prepared in high yield by reaction of the corresponding amino sugars with thiophosgene. In the absence of base, all isothiocyanates were stable and could be stored and acetylated without decomposition. In the presence of triethylamine, 6,6'-dideoxy-6,6'diisothiocyanato-a,a'-trehalose underwent intramolecular cyclisation involving HO-4 to give the corresponding bis(cyclic thiocarbamate). The product of cyclisation at a single glucopyranosyl unit was obtained in the treatment of the above diisothiocyanate with mixed (H +, HO-) ion-exchange resin. Under identical reaction conditions, 6,6'-dideoxy-6,6'-diisothiocyanatosucrose yielded exclusively the product of intramolecular cyclisation at the D-glucopyranosyl moiety, while derivatives of a-D-fructofuranose fl-D-fructopyranose 1,2' :2,1'-dianhydride and cyclomaltooligosaccharides remained unchanged.

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