New supramolecular host systems. 5. Diacetals and macro-m-cyclophanes of aldaric esters: Synthesis, stereochemistry and conformational analysis

Harald Jatzke, Klaus Frische, Moshe Greenwald, Larisa Golender, Benzion Fuchs

Research output: Contribution to journalArticlepeer-review

Abstract

A general scheme of carbohydrate diacetal systems (Scheme 2) of the 1,3,5,7-tetraoxadecalin (TOD) type is presented. A sequence of reactions starting with dimethyl D-glucarate (4) (Scheme 3) lead to 2,6-diaryl-4,8-di (methoxycarbonyl)-cis-TOD podands (5 and 6) and to the novel dicarbamate macrocycles (8a,b), which constitute the first m-cyclophanes in the carbohydrate (D-gluco) series. The D-gluco-L-ido interconversion by equilibration of the methoxycarbonyl groups in 5, 6 and 9, was examined in the light of a conformational analysis of the methoxycarbonyl group and its anomeric effect in heterocyclic systems, using molecular mechanics techniques (MM3-GE, i.e., MM3 reparametrized for treatment of the gauche effect) and comparing with experimental data.

Original languageEnglish
Pages (from-to)4821-4834
Number of pages14
JournalTetrahedron
Volume53
Issue number13
DOIs
StatePublished - 31 Mar 1997

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