Synthesis of Ribonucleosidic Dimers with an Amide Linkage from D-Xylose - Chimie Et Interdisciplinarité : Synthèse, Analyse, Modélisation Accéder directement au contenu
Article Dans Une Revue Journal of Organic Chemistry Année : 2016

Synthesis of Ribonucleosidic Dimers with an Amide Linkage from D-Xylose

Résumé

An original and efficient stereocontrolled synthesis of ribonucleosidic homo- and heterodimers has been achieved from inexpensive D-xylose. This successful strategy involved the sequential introduction of nucleobases, using two stereocontrolled N-glycosidation reactions, from a common two-furanoside amide-linked scaffold offering the possibility of obtaining any given base sequence. The pertinence of this approach is illustrated through the preparation of the homodimers UU-34 and TT-35 in 18 steps with an excellent overall yield of more than 10% from D-xylose, while the heterodimer route led to UT-39 in 19 steps with around 10% overall yield.

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Chimie
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Dates et versions

hal-02141340 , version 1 (27-05-2019)

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Citer

Laurence Arzel, Didier Dubreuil, Fabrice Denes, Virginie Silvestre, Monique Mathé-Allainmat, et al.. Synthesis of Ribonucleosidic Dimers with an Amide Linkage from D-Xylose. Journal of Organic Chemistry, 2016, 81 (22), pp.10742-10758. ⟨10.1021/acs.joc.6b01822⟩. ⟨hal-02141340⟩
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