Preparation and reactions of some β-D-Thioglucopyranosides

α‐Acetobromoglucose with lead dithiophenates afforded the corresponding tetra‐O‐acetyl‐β‐D‐thioglucopyranosides 1a and 2a, with thiourea it gave the isothiouronium bromide derivative 3a, and with the potassium salt of 2‐mercapto‐4‐phenyl‐5‐thiono‐1,3,4‐thiadiazoline, the tetra‐O‐acetyl‐β‐D‐thiogluco...

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Veröffentlicht in:Journal für Praktische Chemie 1972, Vol.314 (3-4), p.461-466
Hauptverfasser: Abdel-Bary, Hamed M. A., Abdel-Megeid, Farouk M. E., El-Hewehi, Zaki, Elkaschef, Mohamed A.-F.
Format: Artikel
Sprache:eng
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Zusammenfassung:α‐Acetobromoglucose with lead dithiophenates afforded the corresponding tetra‐O‐acetyl‐β‐D‐thioglucopyranosides 1a and 2a, with thiourea it gave the isothiouronium bromide derivative 3a, and with the potassium salt of 2‐mercapto‐4‐phenyl‐5‐thiono‐1,3,4‐thiadiazoline, the tetra‐O‐acetyl‐β‐D‐thioglucopyranoside 5a. Hydrolysis of 1a and 2a with barium hydroxide and of 5a with ammonia afforded 1b, 2b, and 5b respectively. Using methyl‐ or ethyl‐amine, for the first time, for hydrolysis, compound 5b was obtained in a higher yield. Oxidation of the tetra‐O‐acetyl‐β‐D‐thioglucopyranosides afforded the corresponding sulphones.
ISSN:0021-8383
1521-3897
DOI:10.1002/prac.19723140311