title: Synthesis of Ribonucleosidic Dimers with an Amide Linkage from d-Xylose.
abstract: 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.
authors: Université de Nantes , CEISAM-UMR CNRS 6230, Faculté des Sciences et des Techniques, 2 rue de la Houssinière, BP 92208, 44322 Nantes Cedex 3, France.
authors: Laurence
authors: L
authors: Arzel
authors: Université de Nantes , CEISAM-UMR CNRS 6230, Faculté des Sciences et des Techniques, 2 rue de la Houssinière, BP 92208, 44322 Nantes Cedex 3, France.
authors: Didier
authors: D
authors: Dubreuil
authors: Université de Nantes , CEISAM-UMR CNRS 6230, Faculté des Sciences et des Techniques, 2 rue de la Houssinière, BP 92208, 44322 Nantes Cedex 3, France.
authors: Fabrice
authors: F
authors: Dénès
authors: Université de Nantes , CEISAM-UMR CNRS 6230, Faculté des Sciences et des Techniques, 2 rue de la Houssinière, BP 92208, 44322 Nantes Cedex 3, France.
authors: Virginie
authors: V
authors: Silvestre
authors: Université de Nantes , CEISAM-UMR CNRS 6230, Faculté des Sciences et des Techniques, 2 rue de la Houssinière, BP 92208, 44322 Nantes Cedex 3, France.
authors: Monique
authors: M
authors: Mathé-Allainmat
authors: Université de Nantes , CEISAM-UMR CNRS 6230, Faculté des Sciences et des Techniques, 2 rue de la Houssinière, BP 92208, 44322 Nantes Cedex 3, France.
authors: Jacques
authors: J
authors: Lebreton