Convenient strategies for the synthesis of 1,4-phenylene spaced sugars

Two synthetic strategies have been developed for the synthesis of spaced sugars with lipophilic 1,4-phenylene core. A building block combining the usefulness of Weinreb amide functionality and modified Julia olefination reaction has been explored towards this objective. This building block offers complete flexibility in attaching any desired sugar derivative across phenylene spacer via C–C bond formation. The other strategy uses carbohydrate based building blocks for the synthesis of symmetrical as well as unsymmetrical 1,4-phenylene spaced sugars. This is the first report for the synthesis of 1,4-phenylene spaced sugars via C–C bond formation.

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► Synthesis of hitherto unreported 1,4-phenylene spaced sugars has been achieved.
► The strategies have versatility to synthesize symmetrical and unsymmetrical varieties.
► Convenience of Weinreb amide group and modified Julia reaction has been used.