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The synthesis and properties of some long-chain alkyl-D-glucofuranosidurono-6,3-lactones, D-glucofuranosides and derivatives thereof

✍ Scribed by Harry W. C. Raaijmakers; Binne Zwanenburg; Gordon J. F. Chittenden

Book ID: 104589608
Publisher: Elsevier Science
Year: 2010
Tongue: English
Weight: 821 KB
Volume: 113
Category: Article
ISSN: 0165-0513
DOI: 10.1002/recl.19941130203

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✦ Synopsis

Abstract

Several long‐chain alkyl‐D‐glucofuranosidurono‐6,3‐lactones were synthesized by the acid‐catalysed glycosidation of glucurono‐6,3‐lactone. The alkyl β‐D‐glucofuranosidurono‐6,3‐lactones were reacted with sodium borohydride to give the corresponding alkyl β‐D‐glucofuranosides, and with 2‐aminoethanol and N,N‐dimethylethanediamine to give the corresponding alkyl‐N‐(2‐hydroxyethyl)‐β‐D‐glucofuranosiduronamides and alkyl‐N‐[2‐(dimethylamino)ethyl]‐β‐D‐glucofuranosiduronamides, respectively. The dodecyl‐N‐[2‐(dimethylamino)ethyl]‐β‐D‐glucofuranosiduronamides were quaternized with iodomethane to give the ammonium iodides. These new compounds, and some representative derivatives, were characterised by ^1^H‐ and ^13^C‐NMR spectroscopy. The physical properties (liquid‐crystal behaviour, surface tension, CMC) of some of these compounds were also determined.

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