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US 8,148,505 B2Granted
Method of α-selective glycosylation
AssigneeJapan Science and Technology Agency
InventorsHiromune Ando, Akihiro Imamura, Makoto Kiso, Hideharu Ishida
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AssigneeJapan Science and Technology Agency
InventorsHiromune Ando, Akihiro Imamura, Makoto Kiso, Hideharu Ishida
Estimating the term…
An α-selective glycosylation process of a glycosylation reaction between a sugar structure of hexose or an aldose having a chain with six or more carbon atoms in the molecule, which is a monosaccharide or a reducing end of an oligosaccharide with two or more monosaccharide residues connected by glycosidic linkages (an oligosaccharide with two monosaccharide residues is disaccharide) (also referred to as “a disaccharide to an oligosaccharide”) or a sugar chain and alcoholic hydroxyl group or thiol group, to obtain a sugar structure glycoside containing α-glycoside at a high ratio, under the ring-shaped formation of a protective group in a silyl acetal structure over hydroxyl groups at positions 4 and 6 in the sugar structure. By the process, highly selective α-glycosylation of sugar structure can be progressed in a simple and efficient manner.
An α-selective glycosylation process between a donor compound having a sugar structure and an acceptor compound having an alcoholic hydroxyl group or thiol group comprising, (1) the step of providing a sugar structure of hexose or an aldose having a chain with six carbon atoms in the molecule which is a monosaccharide or a reducing end of an oligosaccharide having two or more monosaccharide residues or a sugar chain, which sugar structure satisfies the constitutional conditions such that the sugar structure has hydroxyl groups at positions 4 and 6 and that the hydroxyl group at position 4 is in an axial bond and a group at position 5 is in equatorial bond, wherein the sugar structure is substituted with amino at position 2, the amino being bound to a 2,2,2-trichloroethoxycarbonyl group, the sugar structure having a hydroxyl group at the 3-position that is protected with a group selected from among an acetyl group, a benzoyl group, a pivaloyl group, a benzyl group, a p-methoxybenzyl group and an allyl group,
A process for glycosylation of a glycosylation acceptor having an alcoholic hydroxyl group or a thiol group with a glycosylation donor, wherein
An α-selective glycosylation process comprising promoting glycosylation between a sugar structure and an acceptor compound, wherein the sugar structure is substituted with amino at position 2, the amino being bound to a 2,2,2-trichloroethoxycarbonyl group, the sugar structure having hydroxyl groups at positions 4 and 6, and having a protective group of a silyl acetal structure in a ring shape over the hydroxyl groups at positions 4 and 6.
A process for the glycosylation of a glycosylation acceptor comprising promoting the glycosylation between a glycosylation donor comprising a pyranoside structure and a glycosylation acceptor, wherein the pyranoside structure is substituted with amino at the 2-position that is bound to a 2,2,2-trichloroethoxycarhonyl group, and having a cyclic silyl acetal group bridging an equatorially-positionable hydroxy group at 4-position of the pyranoside structure and a hydroxyl group of the axially-positionable hydroxymethyl or hydroxymethylene group at the 5-position of the pyranoside structure so as to form a bicyclo [6.6.0.] structure.
Dependencies are inferred from the claim text.