Carbohydrate Research p. 101 - 116 (1984)
Update date:2022-08-02
Topics:
Gomez-Sanchez, Antonio
Moya, Pastora Borrachero
Bellanato, Juana
2-Deoxy-2-<(2,2-dimethoxycarbonylvinyl)amino>- (1) and 2-deoxy-2-<(2,2-diethoxycarbonylvinyl)amino>-α-D-glucopyranose (3), prepared in almost quantitative yields from the appropriate 3-alkoxy-2-alkoxycarbonylacrylic ester and 2-amino-2-deoxy-D-glucose hydrochloride, were used as N-protected derivatives in the preparation of glycosides by the Fischer procedure.Glycosidation of 1 with boiling methanolic hydrogen chloride afforded a mixture of methyl 2-deoxy-2-<(2,2-dimethoxycarbonylvinyl)amino>-α- (7α) and -β-D-glucopyranoside (7β), and minor amounts of methyl 2-deoxy-2-<(2,2-dimethoxycarbonylvinyl)amino>-α-D-glucofuranoside (18); 7α was easily isolated (55percent yield).Using Amberlyst-15 (H1+) resin as catalyst, the proportion of the furanoside 18 was higher and 21percent could be isolated.Reaction of 3 with hot ethanolic hydrogen chloride afforded a good yield of ethyl 2-deoxy-2-<(2,2-diethoxycarbonylvinyl)amino>-α-D-glucopyranoside.On the other hand, attempted glycosidations of 2-deoxy-2-<(2,2-diacetylvinyl)amino>-α-D-glucopyranose under similar conditions were unsuccesfull.The 2,2-diacylvinyl group could be removed selectively under non-acidic conditions using chlorine, ammonia, or Amberlite IRA-400 (HO1-) resin.
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Doi:10.1246/bcsj.80.1995
(2007)Doi:10.1071/CH99098
(1999)Doi:10.1021/jo9915729
(2000)Doi:10.1039/b000411l
(2000)Doi:10.1246/cl.1992.1469
(1992)Doi:10.1246/cl.2000.204
(2000)