Synthesis and properties of sulfated alkyl glycosides.
Carbohydr Res
; 230(2): 245-56, 1992 Jun 16.
Article
in En
| MEDLINE
| ID: mdl-1394299
ABSTRACT
Alkyl glycosides were sulfated with sulfur trioxide-pyridine. Dodecyl alpha- and beta-D-glucopyranoside gave the corresponding 6-sulfates in 75 and 51% yields, respectively. Separation from polysulfated compounds was carried out by reversed-phase HPLC. Tetradecyl beta-maltopyranoside (16) gave a 88 12 mixture of 6'- and 6-sulfates. The sulfated compounds were characterized by 1H-, 13C-, and 2-dimensional NMR spectroscopy. Surfactant and thermotropic liquid-crystalline properties of the sugar derivatives were examined. All of the glycosides show smectic phases (SA), and the clearing points rise by introduction of sulfate groups. Even glycosides having no unprotected hydroxy groups may show SA-phases when bearing sulfate groups. The mesomorphic properties cannot be explained by formation of distinct aggregates, but rather must be interpreted by an effective intramolecular contrast.
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Collection:
01-internacional
Database:
MEDLINE
Main subject:
Glycosides
Language:
En
Journal:
Carbohydr Res
Year:
1992
Document type:
Article
Affiliation country:
Germany