Tetrahedron

Synthesis of macrocyclic acetals containing lipophilic substituents

JS Bradshaw, KE Krakowiak, GC LindH, RM Izatt

Index: Bradshaw, Jerald S.; Krakowiak, Krzysztof E.; LindH, Gypzy C.; Izatt, Reed M. Tetrahedron, 1987 , vol. 43, # 19 p. 4271 - 4276

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Citation Number: 24

Abstract

A series of new macrocyclic acetals all containing lipophilic substituents were prepared by reacting the appropriate diols and lipophilic acetal-containing dichlorides or ditosylates. The reactions using the ditosylates gave the best yields. Several of the macrocycles contained pyridine subcyclic units. The lipophilic acetals were obtained by reacting a long-chain aldehyde with 2-hydroxyethyl chloride or tosylate and 3-hydroxypropyl chloride or tosylate ...