Solution and solid phase sulfoxide glycosylation: synthesis...

G - Physics – 01 – N

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G01N 33/53 (2006.01) C07G 3/00 (2006.01) C07G 11/00 (2006.01) C07H 1/00 (2006.01) C07H 5/10 (2006.01) C07H 15/00 (2006.01) C07H 15/12 (2006.01) C07H 17/00 (2006.01) G01N 33/543 (2006.01) G01N 33/566 (2006.01) C07B 61/00 (2006.01)

Patent

CA 2319339

The invention relates to a process for the synthesis of .beta.- oligosaccharides. .beta.-oligosaccharides are synthesized using alkylsulfenyl- or an arylsulfenyl-2-deoxy-2-N-trifluoroacetamidoglycopyranoses as glycosyl donors via the sulfoxide glycosylation, both in solution and solid phases. Once activated under the glycosylation conditions, these donors afford the respective .beta.-glycosides exclusively and in high yield. Since the trifluoroacetamido group is easily removed under mild conditions, the corresponding amino group can be appropriately derivatized, even in the presence of unprotected hydroxyl groups. Disaccharide libraries are designed, constructed and analyzed. The invention also relates to a process for synthesizing the glycosyl donor.

La présente invention concerne un procédé de synthèse de .beta.-oligosaccharides, dans lequel on utilise des alkylsulfényl- ou arylsulfényl-2-déoxy-2-N-trifluoracétamidoglycopyranoses comme donneurs de glycosyle via la glycosylation du sulfoxyde, à la fois en solution et en phase solide. Une fois activés dans les conditions de glycosylation, ces donneurs produisent les .beta.-glycosides de façon exclusive et avec un rendement élevé. Etant donné que le groupe trifluoroacétamido est facilement éliminé dans des conditions douces, le groupe amino correspondant peut être dérivatisé de manière adéquate, même en présence de groupes hydroxyle non protégés. L'invention concerne la conception, la construction et l'analyse de bibliothèques de disaccharides, ainsi qu'un procédé permettant de synthétiser le donneur de glycosyle.

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