Chiral Perfluoroalkyl‐Substituted Hexahydrofuro[2,3‐ b ]pyran Derivatives Based on a Carbohydrate Precursor

(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.