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Amphiphilic Carbohydrate‐based Mesogens, IX. Mesogenic 4‐ O ‐Alkyl‐ D ‐glucoses via Methyl 4,6‐ O ‐Alkylidene‐ D ‐glucopyranosides
Author(s) -
Dahlhoff Wilhelm V.,
Riehl Klaus,
Zugenmaier Peter
Publication year - 1993
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.1993199301171
Subject(s) - chemistry , mesogen , alkyl , pyridinium , hydrolysis , amphiphile , yield (engineering) , condensation , stereochemistry , organic chemistry , medicinal chemistry , polymer chemistry , phase (matter) , liquid crystalline , copolymer , polymer , materials science , metallurgy , thermodynamics , physics
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.