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Amphiphilic carbohydrate-based mesogens, VII. Synthesis of mesogenic 4- and 6-O-alkyl-D-glucitols

✍ Scribed by Dahlhoff, Wilhelm V.

Publisher
John Wiley and Sons
Year
1991
Tongue
English
Weight
488 KB
Volume
1991
Category
Article
ISSN
0947-3440

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✦ Synopsis

Abstract

Both the hemiacetal and acetal groups of 4,6‐O‐alkylidene‐α/β‐D‐glucopyranoses (hexylidene–decylidene, 1a–e) are quantitatively reduced by ethyldiboranes(6) in the presence of 9‐methylsulfonyloxy‐9‐borabicyclo[3.3.1]nonane (MSBBN) after conversion to their 1,2,3‐tri‐O‐diethylboryl derivatives 2a–e. Subsequent deboronations give ca. 1:1 mixtures of 4‐O‐alkyl‐D‐glucitols 3a–e and 6‐O‐alkyl‐D‐glucitols 4a–e, which are separated to give mesogenic 3 and 4. Both 3 and 4 exhibit smectic A liquid crystalline phases.

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## Abstract Alkyl 1‐thio‐α,β‐D‐glucopyranosides (hexyl to decyl, 1a–e) are prepared by reaction of penta‐__O__‐acetyl‐β‐D‐glucopyranose with the respective thiols in the presence of diethyl ether — trifluoroborane, followed by deacetylation. 1a–e are converted into their tetra‐__O__‐diethylboryl de