Tetrahedron p. 6235 - 6250 (1993)
Update date:2022-09-26
Topics:
Fuentes
Cuevas
Angeles Pradera
The syntheses of ethyl 3,4-di-O-acyl(benzyl)-2-benzyloxycarbonylamino-2-deoxy-6-O-trityl-α-D -glucopyranosides (2-4) and methyl 3,4-di-O-acyl(benzyl)-2-deoxy-2-[(2',2'-dimethoxycarbonylvinyl)amino]- 6-O-trityl-]-α-D-glucopyranosides (12-14) are reported. The partially protected D-glucosamine derivatives ethyl 3,4-di-O-benzyl- (5) and 3-benzyl-2-benzyloxycarbonylamino-2-deoxy-α-D-glucopyranoside (6), ethyl 3,4-di-O-benzoyl-2-benzyloxycarbonylamino-2-deoxy-α-D-glucopyranoside (9), methyl 3,4-di-O-acyl(benzyl)-2-deoxy-2-dimethoxycarbonylvinylamino-α-D-gluco pyranosides (15-17) have been prepared or isolated as by-products. The preparation of ethyl 3,4-di-O-acetyl- (18), 3,4-di-O-benzoyl- (19), and 3,4-di-O-benzyl-2-benzyloxycarbonylamino-2-deoxy-6-O-(2,3,4,6-tetra-O- acetyl-β-D-glucopyranosyl)-α-D-glucopyranosides (20), and methyl 3,4-di-O-acetyl- (21), 3,4-di-O-benzoyl- (22), and 3,4-di-O-benzyl-2-deoxy-2-dimethoxycarbonylamino-6-O-(2,3,4,6-tetra-O- acetyl-β-D-glucopyranosyl)-α-D-glucopyranosides (23) through glycosylation reactions using 2, 3, 4, 12, 13, and 14 resepctively as glycosyl acceptors and acetobromoglucose as glycosyl donor is described. The N-protecting group of 18, 19, and 21 was removed to give the alkyl hexa-O-acyl-2-amino-2-deoxy gentiobioside hydrohalides 24-26 respectively.
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Doi:10.1021/ic4026987
(2014)Doi:10.1021/acs.jmedchem.1c00047
(2021)Doi:10.1111/1467-954X.00241
(1879)Doi:10.1016/S0040-4039(00)91019-0
(1967)Doi:10.1080/07328319308018561
(1993)Doi:10.1002/hlca.19480310650
(1948)