Wiley InterScience Backfile Collection 1832-2000
Chemistry and Pharmacology
(4′R)-4,6-Di-O-acetyl-1,2,3-trideoxy-3-iodo-4′-(2,2,3,3,4,4,5,5,6,6,7,7,8,8,9,9,9-heptadecafluorononyl)-2′,3′,4′,5′-tetrahydro-α-D-glucopyranoso[1,2-b]furan (2) and its (4′S) diastereomer (3) were prepared by dithionite-mediated addition of 1-iodoperfluorooctane to allyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside (radical “domino reaction”). Subsequently, the major product [(4′R) form] was deprotected via 4 to the hexahydrofuro[2,3-b]pyran derivative 5, which was used as a fluorinated building block to prepare the nonamphiphilic chiral mesogens 6-8 by “Mitsunobu” etherification and 9 by esterification. The reagents used to transform 5 to 6-9 were 4-cyanophenol, 4-(4-cyanophenyl)phenol, 4-(4-heptyloxybenzoyloxy)phenol, and 4-heptyloxybenzoyl chloride.
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