A COMPARISON IN THE EFFICIENCY OF 6 STANDARD 2-AMINO-2-DEOXY-GLUCOSYL DONORS FOR THE SYNTHESIS OF (2-DEOXY-2-PHTHALIMIDO-BETA-D-GLUCOPYRANOSYL)(1-]4)-BETA-D-GLUCOPYRANOSIDES

被引：10

作者：

SILWANIS, BA

ELSOKKARY, RI

NASHED, MA

PAULSEN, H

机构：

[1] UNIV ALEXANDRIA,FAC SCI,DEPT CHEM,ALEXANDRIA,EGYPT

[2] UNIV HAMBURG,INST ORGAN CHEM,W-2000 HAMBURG 13,GERMANY

来源：

JOURNAL OF CARBOHYDRATE CHEMISTRY | 1991年 / 10卷 / 06期

关键词：

D O I：

10.1080/07328309108543973

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

A systematic study is presented for the most common methods used for the preparation of the disaccharide benzyl O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-beta-D-glucopyranosyl) -(1 --> 4)-3,6-di-O-benzoyl-2-deoxy-2-phthalimido-beta-D-glucopyranoside (9) from ''standard 2-amino-2-deoxyglucopyranosyl donors'' 1-6 and benzyl 3,6-di-O-benzoyl-2-deoxy-2-phthalimido-beta-D-glucopyranoside (7) as an acceptor. It was found that the highest yield was obtained when the trichloroacetimidate derivative 1 was coupled to the 4 position of acceptor 7. In an analogous manner, the disaccharides allyl O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-beta-D-glucopyranosyl)-(1--> 4)-3, 6,-di-O-benzoyl-2-deoxy-2-phthalimido-beta-D-glucopyranoside (10), benzyl O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-beta-D-glucopyranosyl)-(1 --> 4)-3, 6-di-O-benzoyl-2-deoxy-2-phthalimido-beta-D-galactopyranoside (12), and allyl O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-beta-D-glucopyranosyl)-(1 --> 3)-4, 6-O-benzylidene-2-deoxy-2-phthalimido-beta-D-glucopyranoside (14) were prepared.

引用

页码：1067 / 1078

页数：12

共 22 条

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ANDERSSON F, 1989, ACS SYM SER, V386, P117

[2] SYNTHESIS OF 1,2-CIS-LINKED GLYCOSIDES USING DIMETHYL(METHYLTHIO)SULFONIUM TRIFLATE AS PROMOTER AND THIOGLYCOSIDES AS GLYCOSYL DONORS [J].