Preparation of thioarabinofuranosyl compounds and use thereof

Details Preparation of thioarabinofuranosyl compounds and use thereof Preparation of thioarabinofuranosyl compounds and use thereof

C - Chemistry, Metallurgy

07

H

C07H 19/09 (2006.01) A61P 35/00 (2006.01) C07H 19/06 (2006.01)

Patent

CA 2464681

A method for producing a compound of the formula I: (see formula I) comprises A) reacting a 2,3,5-tri-O-aryl or alkyl-4-xylose diaryl or dialkyl dithioacetal in the presence of a leaving group at the 4 hydroxyl position to produce the corresponding 1,4-dithio-D-arabinofuranoside; B) reacting said arabinofuranoside from step A) to acidolysis to form the corresponding O-acetyl-4-thio-D-arabinofuranose; C) reacting said O-acetyl-4--thio-D-arabinofuranose from step B) with a compound selected from the group consisting of a cytosine, a 5-aza compound, a 6-aza compound and blocked derivatives thereof to form the corresponding 4-thio-.infin., .beta.-D-arabinofuranosyl compound; D) converting said arabinofuranosyl compound from step C) by hydrolysis to the corresponding thio sugar derivative; and E) separating out the .infin. form or the anomeric mixture of step D) to thereby obtain the compound of formula I.

Divulgation d'une méthode de production d'un composé de formule I (voir la formule I) comprenant les étapes suivantes : A) réaction d'un 2,3,5-tri-O-aryle(ou alkyl)-4-xylose-diaryl(ou dialkyl)dithioacétal en présence d'un groupe partant à la position 4-hydroxyle pour produire le 1,4-dithio-D-arabinofuranoside correspondant, B) acidolyse dudit arabinofuranoside obtenu à l'étape A) pour former le O-acétyl-4-thio-D-arabinofuranose correspondant, C) réaction dudit O-acétyl-4-thio-D-arabinofuranose obtenu à l'étape B avec un composé choisi dans le groupe constitué de la cytosine, d'un composé 5-aza-, d'un composé 6-aza- et de dérivés séquencés de ceux-ci pour former le 4-thio-.infin.-.bêta.-D-arabinofuranosyle correspondant, D) conversion dudit arabinofuranosyle obtenu à l'étape C par hydrolyse pour former le thiosucre correspondant, E) séparation de la forme .infin. ou du mélange anomère de l'étape D) pour former le composé de formule I.

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