A novel intramolecular decarboxylative glycosylation via mixed carbonate

被引：34

作者：

Iimori, T ^{[1
]}

Shibazaki, T ^{[1
]}

Ikegami, S ^{[1
]}

机构：

[1] TEIKYO UNIV, FAC PHARMACEUT SCI, SAGAMIKO, KANAGAWA 19901, JAPAN

来源：

TETRAHEDRON LETTERS | 1996年 / 37卷 / 13期

关键词：

D O I：

10.1016/0040-4039(96)00272-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A two-step glycosylation procedure, which involves (1) linking two sugars by using carbonate as a connector, (2) removing carbon dioxide to form a glycosidic bond by the aid of Lewis acid, has been developed. This glycosylation procedure was based on the opposite mode of connection, where a glycosyl acceptor was activated to link sugars.

引用

页码：2267 / 2270

页数：4

共 13 条

[1]

Einhorn A, 1911, LIEBIGS ANN CHEM, V382, P237

[2] SYNTHETIC STUDIES BY USE OF CARBONATES .4. NEW METHODS FOR SYNTHESIS OF GLYCOSYL COMPOUNDS BY USE OF 1-O-ARYLOXYCARBONYL SUGAR DERIVATIVES [J].

INABA, S ;

YAMADA, M ;

YOSHINO, T ;

ISHIDO, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (06) :2062-2063

[3] SYNTHETIC STUDIES WITH CARBONATES .11. D-GLUCOPYRANOSE 1-CARBONATE DERIVATIVES - PYROLYTIC BEHAVIOR AND USE FOR GLUCOSYLATION OF PHENOLS [J].

ISHIDO, Y ;

INABA, S ;

MATSUNO, A ;

YOSHINO, T ;

UMEZAWA, H .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1977, (12) :1382-1390

[4] SYNTHESIS OF GLYCOPEPTIDES, PARTIAL STRUCTURES OF BIOLOGICAL RECOGNITION COMPONENTS [J].

KUNZ, H .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1987, 26 (04) :294-308

[5] ASYMMETRIC DIELS-ALDER REACTION BY THE USE OF A CHIRAL TITANIUM CATALYST WITH MOLECULAR SIEVES-4A - REMARKABLE SOLVENT EFFECT ON THE ENANTIOSELECTIVITY [J].

NARASAKA, K ;

INOUE, M ;

YAMADA, T ;

SUGIMORI, J ;

IWASAWA, N .

CHEMISTRY LETTERS, 1987, (12) :2409-2412

[6] ASYMMETRIC INTRAMOLECULAR ENE REACTION CATALYZED BY A CHIRAL TITANIUM ALKOXIDE [J].

NARASAKA, K ;

HAYASHI, Y ;

SHIMADA, S .

CHEMISTRY LETTERS, 1988, (10) :1609-1612

[7] SYNTHESIS OF VERRUCARIN-B [J].

ROUSH, WR ;

BLIZZARD, TA .

JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (23) :4332-4339

[8] FACILE, HIGHLY SELECTIVE SYNTHESIS OF ALPHA-DISACCHARIDES AND BETA-DISACCHARIDES FROM 1-O-METALATED D-RIBOFURANOSES [J].

SCHMIDT, RR ;

REICHRATH, M .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1979, 18 (06) :466-467

[9] NEW METHODS FOR THE SYNTHESIS OF GLYCOSIDES AND OLIGOSACCHARIDES - ARE THERE ALTERNATIVES TO THE KOENIGS-KNORR METHOD [J].

SCHMIDT, RR .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1986, 25 (03) :212-235

[10] SYNTHESIS OF ALPHA-D-MANNOFURANOSIDES AND BETA-D-MANNOFURANOSIDES VIA 1-0-ALKYLATION [J].

SCHMIDT, RR ;

REICHRATH, M ;

MOERING, U .

TETRAHEDRON LETTERS, 1980, 21 (37) :3561-3564

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