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Annulative Dimerization of Carbohydrates: Synthesis of Complex C 2 ‐Symmetrical 1,4‐Dioxane‐Sugar Hybrids
Author(s) -
RobertScott Gabrielle,
StGelais Jacob,
Giguère Denis
Publication year - 2021
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202100411
Subject(s) - chemistry , sugar , derivatization , carbohydrate , 1,4 dioxane , molecule , carbohydrate chemistry , organic chemistry , combinatorial chemistry , stereochemistry , high performance liquid chromatography
The synthesis of carbohydrate‐heterocycle hybrid molecules has led to several interesting biologically active products. In this work, we have developed an annulative process for the formation of novel C 2 ‐symmetrical 1,4‐dioxane‐carbohydrate hybrid compounds. Starting from simple sugars, original 6‐6‐6 heterocyclic frameworks were isolated. The dioxane units adopted a rare 1,4 twist‐boat conformations in the liquid and solid‐states. Synthetic derivatization allowed the preparation of C 2 ‐symmetrical glycomimetics that could be used for further biological investigations.