Synthesis of Per- and Poly Substituted Trehalose Derivatives: Studies of Properties Relevant to Their Use as Excipients for Controlled Drug Release

Thomas C Baddeley, James L Wardell

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Per- and poly-substituted oligosaccharide derivatives, with trehalose cores, have been prepared and assessed for their potential for use as excipients in controlled-release formulations. The synthesized compounds, generally with acyl and amido substituents, included 6,6′-N,N′ -diamido-6,6′ -dideoxy-α,α -trehalose derivatives, 6,6′ -bis(1,2,3,4-tetra-O-acetyl-β -D-glucopyranuronyl)-α, α -trehalose derivatives, 2,2′,3,3′ -tetra-O-acetyl-6,6′ -bis-(1,2,3,4-tetra-O-acetyl-β-D-glucopyranuronyl)-4,4′ -di-O-acyl-α,α-trehalose, 2, 2′, 3, 3′ -tetra-O-acetyl-6-(1,2,3,4-tetra-O-acetyl-β-D-glucopyranuronyl)-4,4′,6′ -tri-O-acyl-α,α-trehalose, and 2,2′,3,3′,4,4′ -hexa-O-acetyl-6,6′ -bis-(1,2,3,4-tetra-O-acetyl-6-O-succinyl-β-D-glucopyranuronyl)-α,α-trehalose. Compounds were characterized by NMR, IR, MS and optical rotations; elemental analyses; or HRMS. The compounds formed amorphous materials either on fast quenching of melts or on spray drying. Properties, used in the initial assessment of the potential as controlled-release excipients, were log10 P and glass transition, Tg, values.
Original languageEnglish
Pages (from-to)198-221
Number of pages24
JournalJournal of Carbohydrate Chemistry
Issue number4
Publication statusPublished - May 2009


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