ISSN:
0170-2041
Keywords:
Carbohydrates
;
Liquid crystals
;
1-Thio-α,β-D-glucopyranosides
;
Glucitol derivatives
;
Glycoside hydroboration
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
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 derivatives 2a-e and reduced with ethyldiboranes(6) in the presence of the catalyst 9-methylsulfonyloxy-9-borabicyclo[3.3.1]nonane (9-BBN-mesylate, MSBBN) to give the mesogenic 1-alkylthio-1-deoxy-D-glucitols 3a-e after deboronation.
Additional Material:
1 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.1990199001185
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