ISSN:
0170-2041
Keywords:
Carbohydrates
;
4-O-Alkyl-D-glucoses
;
Liquid crystals, smectic
;
Bromodiethylborane-sodium triethylhydroborate reducing system
;
Amphiphilic glucoses
;
X-ray diffraction, small angle
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
The 4,6-O-alkylidene derivatives (hexylidene-decylidene, 2a-e) are prepared by condensation of methyl α- or β-D-glucopyranoside 1 with alkanals in the presence of pyridinium tosylate. O-diethylborylation of 2 gives 3 which are allowed to react firstly with bromodiethylborane and subsequently with sodium triethylhydroborate to yield methyl 4-O-alkyl-D-glucopyranosides 5 after deborylation. Acid hydrolysis of 5 gives mesogenic 4-O-alkyl-D-glucopyranoses 6a-e. The amphiphilic 6 exhibit the smectic A liquid crystalline phase on melting.
Additional Material:
1 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.1993199301171
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