PREPARATION OF ETHER-LINKED 2-ACETAMIDO-2-DEOXY BETA-GLYCOLIPIDS VIA ZINC-CHLORIDE PROMOTED COUPLING OF AC(4)GLCNAC-CL WITH LIPID HYDROXY-GROUPS

被引：10

作者：

KUMAR, ER ^{[1
]}

BYUN, HS ^{[1
]}

WANG, SH ^{[1
]}

BITTMAN, R ^{[1
]}

机构：

[1] CUNY QUEENS COLL,DEPT CHEM & BIOCHEM,FLUSHING,NY 11367

来源：

TETRAHEDRON LETTERS | 1994年 / 35卷 / 04期

关键词：

D O I：

10.1016/S0040-4039(00)75823-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Stereoselective glycosidation of lipid hydroxy groups has been achieved using 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-alpha-D-glycosyl chloride as the glycosyl donor in CH2Cl2. In the presence of ZnCl2 (1 equiv.) and various ''promoters'' (1 equiv.) such as Ph(3)CCl, 18-crown-6/KCl, n-Bu(4)NBr, or Me(3)SiCl, beta-glycolipid conjugates are formed as the initial products, but they undergo anomerization on prolonged reaction times. The promoters may enhance the solubility of ZnCl2 in CH2Cl2.

引用

页码：505 / 508

页数：4

共 7 条

[1]

[Anonymous], ORGANIC SYNTHESES CO

[2] SYNTHESIS AND ANTINEOPLASTIC PROPERTIES OF ETHER-LINKED THIOGLYCOLIPIDS [J].

GUIVISDALSKY, PN ;

BITTMAN, R ;

SMITH, Z ;

BLANK, ML ;

SNYDER, F ;

HOWARD, S ;

SALARI, H .

JOURNAL OF MEDICINAL CHEMISTRY, 1990, 33 (09) :2614-2621

[3] NOVEL STEREOSELECTIVE GLYCOSIDATION BY THE COMBINED USE OF TRITYL HALIDE AND LEWIS ACID [J].

HIGASHI, K ;

NAKAYAMA, K ;

SOGA, T ;

SHIOYA, E ;

UOTO, K ;

KUSAMA, T .

CHEMICAL & PHARMACEUTICAL BULLETIN, 1990, 38 (12) :3280-3282

[4] SYNTHESIS OF PARA-TRIFLUOROACETAMIDOPHENYLETHYL O-(2-ACETAMIDO-2-DEOXY-BETA-D-GALACTOPYRANOSYL)-(1-]4)-O-BETA-D-GALACTOPYRANOSYL-(1-]4)-O-BETA-D-GLUCOPYRANODISE, CONTAINING THE TRISACCHARIDE PORTION OF THE ASIALO-GM2 GLYCOLIPID [J].

KALLIN, E ;

LONN, H ;

NORBERG, T .

JOURNAL OF CARBOHYDRATE CHEMISTRY, 1990, 9 (05) :721-733

[5] SOME IMPLICATIONS IN CARBOHYDRATE CHEMISTRY OF THEORIES RELATING TO THE MECHANISMS OF REPLACEMENT REACTIONS [J].

LEMIEUX, RU .

ADVANCES IN CARBOHYDRATE CHEMISTRY, 1954, 9 :1-57

[6] A FACILE SYNTHESIS OF ALPHA-GLUCOSIDES AND ALPHA-RIBOSIDES FROM THE CORRESPONDING 1-O-ACYL SUGARS AND ALCOHOLS IN THE PRESENCE OF TRITYL PERCHLORATE [J].

MUKAIYAMA, T ;

KOBAYASHI, S ;

SHODA, S .

CHEMISTRY LETTERS, 1984, (06) :907-910

[7]

SZABO L, 1993, IN PRESS CARBOHYDR R

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