A NOVEL, REGIOSELECTIVE AND HIGHLY STEREOSELECTIVE ANOMERIC DEACETYLATION OF 2-AMINOSUGAR DERIVATIVES

被引：15

作者：

AVALOS, M

BABIANO, R

CINTAS, P

JIMENEZ, JL

PALACIOS, JC

VALENCIA, C

机构：

[1] Departamento de Química Orgánica, Facultad de Ciencias, Universidad de Extremadura

来源：

TETRAHEDRON LETTERS | 1993年 / 34卷 / 08期

关键词：

D O I：

10.1016/S0040-4039(00)91795-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Silica gel-mediated anomeric deacetylation of per-acetylated 2-amino-2-deoxy-glycopyranose derivatives in methanol constitutes a mild and inexpensive protocol for the selective deprotection of these relevant carbohydrate templates. The reaction proceeds with high stereoselectivity and with an almost complete avoidance of by-products.

引用

收藏

页码：1359 / 1362

页数：4

相关论文

共 35 条

[1] A NEW, EFFICIENT METHOD FOR HYDROLYSIS OF THE ANOMERIC ACETYL GROUP IN SUBSTITUTED HEXOPYRANOSES [J].

BANASZEK, A ;

CORNET, XB ;

ZAMOJSKI, A .

CARBOHYDRATE RESEARCH, 1985, 144 (02) :342-345

[2] ISOMERS OF TETRA-O-ACETYL-D-MANNOPYRANOSE [J].

BONNER, WA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1958, 80 (13) :3372-3379

[3]

CAREY FA, 1990, ADV ORGANIC CHEM A, P152

[4] SELECTIVE CLEAVAGE OF ANOMERIC ACETYL GROUPS OF ACETYLATED GLYCOSYL RESIDUES BY HYDRAZINE [J].

EXCOFFIER, G ;

GAGNAIRE, D ;

UTILLE, JP .

CARBOHYDRATE RESEARCH, 1975, 39 (02) :368-373

[5]

FIANDOR J, 1985, SYNTHESIS-STUTTGART, P1121

[6]

Garcia Gonzalez F., 1965, CARBOHYD RES, V1, P261

[7] On the 2,3,4,6-tetra-acetyl-d-glucoses alpha and beta and on a new source of error in the determination of fusion points in capillary tubing [J].

Georg, A .

HELVETICA CHIMICA ACTA, 1932, 15 :924-935

[8]

GONZALEZ FG, 1967, CARBOHYD RES, V3, P486

[9] SYNTHESES OF "2,3,6-TRIDEOXY-3-AMINO-NITROHEXOSES AND 2,3,6-TRIDEOXY-3-NITROHEXOSES [J].

HAUSER, FM ;

ELLENBERGER, SR .

CHEMICAL REVIEWS, 1986, 86 (01) :35-67

[10] ENZYMES IN CARBOHYDRATE SYNTHESIS - LIPASE-CATALYZED SELECTIVE ACYLATION AND DEACYLATION OF FURANOSE AND PYRANOSE DERIVATIVES [J].

HENNEN, WJ ;

SWEERS, HM ;

WANG, YF ;

WONG, CH .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (21) :4939-4945

← 1 2 3 4 →