Environmentally compatible C-glycosidation of glycals using montmorillonite K-10

被引：46

作者：

Toshima, K

Miyamoto, N

Matsuo, G

Nakata, M

Matsumura, S

机构：

[1] Department of Applied Chemistry, Faculty of Science and Technology, Keio University, Kohoku-ku, Yokohama 223

来源：

CHEMICAL COMMUNICATIONS | 1996年 / 11期

关键词：

D O I：

10.1039/cc9960001379

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The C-glycosidations of glycal acetates 1-4 with allyltrimethylsilane 5, vinyloxytrimethylsilane 6 or isopropenyl acetate 7 using montmorillonite K-10 as an environmentally acceptable and inexpensive industrial catalyst under mild conditions proceed effectively to give the corresponding 2,3-unsaturated C-glycosides in high yields.

引用

页码：1379 / 1380

页数：2

共 17 条

[1]

[Anonymous], 1993, ORGANIC CHEM USING C

[2] SYNTHESIS OF C-DISACCHARIDES [J].

BABIRAD, SA ;

WANG, Y ;

KISHI, Y .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (07) :1370-1372

[3] ON THE ADDITION OF ALLYLTRIMETHYLSILANE TO GLYCAL ACETATES [J].

DANISHEFSKY, S ;

KERWIN, JF .

JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (19) :3803-3805

[4]

Ferrier R J, 1969, Adv Carbohydr Chem Biochem, V24, P199

[5] UNSATURATED CARBOHYDRATES .9. SYNTHESIS OF 2,3-DIDEOXY-ALPHA-D-ERYTHRO-HEX-2-ENOPYRANOSIDES FROM TRI-O-ACETYL-D-GLUCAL [J].

FERRIER, RJ ;

PRASAD, N .

JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1969, (04) :570-&

[6] SOME PROGENY OF 2,3-UNSATURATED SUGARS - THEY LITTLE RESEMBLE GRANDFATHER GLUCOSE - 10 YEARS LATER [J].

FRASERREID, B .

ACCOUNTS OF CHEMICAL RESEARCH, 1985, 18 (11) :347-354

[7] USE OF UNSATURATED SUGARS AS ALKYLATING-AGENTS - ADDITION OF ENOL ESTERS AND ETHERS TO GLYCALS [J].

GRYNKIEWICZ, G ;

BEMILLER, JN .

JOURNAL OF CARBOHYDRATE CHEMISTRY, 1982, 1 (02) :121-127

[8]

Hacksell U, 1985, Prog Med Chem, V22, P1, DOI 10.1016/S0079-6468(08)70228-5

[9] SYNTHESIS OF C-GLYCOSYL COMPOUNDS FROM 3,4,6-TRI-O-ACETYL-1,5-ANHYDRO-D-ARABINO-HEX-1-ENITOL AND ALLYLTRIMETHYLSILANE AND BIS(TRIMETHYLSILYL)ACETYLENE [J].

ICHIKAWA, Y ;

ISOBE, M ;

KONOBE, M ;

GOTO, T .

CARBOHYDRATE RESEARCH, 1987, 171 :193-199

[10]

IZUMI Y, 1992, ZEOLITE CLAY HETEROP, P21

← 1 2 →