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Amphiphilic carbohydrate‐based mesogens, VII . Synthesis of mesogenic 4‐ and 6‐ O ‐alkyl‐ D ‐glucitols
Author(s) -
Dahlhoff Wilhelm V.
Publication year - 1991
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.199119910184
Subject(s) - mesogen , chemistry , alkyl , hemiacetal , acetal , amphiphile , stereochemistry , organic chemistry , polymer chemistry , medicinal chemistry , liquid crystalline , copolymer , phase (matter) , polymer
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.