The Synthesis of the 3′- and 3′′′-Monodeoxygenated Derivatives of β-Maltosyl-(1→4)-Trehalose
Autor: | Rudolf E. Minder, Hans Peter Wessel |
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Rok vydání: | 1997 |
Předmět: | |
Zdroj: | Journal of Carbohydrate Chemistry. 16:807-829 |
ISSN: | 1532-2327 0732-8303 |
DOI: | 10.1080/07328309708006542 |
Popis: | Two derivatives of β-maltosyl-(1→4)-trehalose monodeoxygenated at C-3′ or C-3′′′ have been synthesized in [2+2] block syntheses. Starting from 4,6;4′,6′-di-O-benzylidene-trehalose (3) the 3′-hydroxyl group was singled out by selective pivaloylation and reduced by a Barton-McCombie reaction. The benzylidene group in the vicinity of the deoxy function could be reductively opened to supply a suitable monodeoxygenated glycosyl acceptor (8). Standard glycosylation with hepta-O-acetylmaltosyl bromide and deprotection led to 3′-deoxymaltosyl-(1→4)-trehalose 13. For the synthesis of a 3′-deoxygenated derivative of maltose we used 1,6-anhydromaltose as starting material. From the tributyltin hydride reduction of the 3,3′-bis-thiocarbonylimidazole derivative 18, the 3′-monodeoxygenated derivative 20 was obtained in low yield. After opening of the 1,6-anhydro ring, the maltosyl derivative was activated as trichloroacetimidate 24. Glycosylation followed by standard deprotection furnished the 3′′′-deoxymaltos... |
Databáze: | OpenAIRE |
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