Synthesis of C2-symmetric carbohydrate-based macrocycles by introduction of methylene/p-xylene linkers

Abstract

Over the last few decades many carbohydrate embedded macrocycles have drawn the attention of synthetic organic chemists because of their interesting chemical and biological properties. Suitably placed chiral 3-and 5-hydroxyl groups of 1,2-O-(1-methylethylidene)-α-D-xylofuranose, derived from inexpensive D-glucose, have been judiciously exploited to generate different non-natural C2-symmetric carbohydrate embedded macrocycles. Different symmetric aromatic and aliphatic hydrophobic spacers have been introduced between highly functionalized cluster of carbohydrate chiral centres through different intra-and intermolecular nucleophilic substitution and ring closing metathesis (RCM) for synthesis of 17 to 24 membered C2-symmetric macrocycles.

Transglycosylation Reaction: Synthesis and Supramolecular Study of Carbohydrate‐Cased C2‐Symmetric 20‐ and 22‐Membered Macrocyclic Dinucleosides

“…Among four previously synthesised C 2 –symmetric macrocycles ( CSM‐1 , CSM‐2 , CSM‐3 and CSM‐4 ) [42] (Figure 2), two can be successfully converted to purine and pyrimidine appended C 2 ‐symmetric [43] macrocyclic dinucleosides. From CSM‐3 we have been able to make 3 , 4 , 5 , 6 , 7 and from CSM‐4 also the attempted synthesis of 16 was successful.…”