REGIOSELECTIVE BROMINATION OF O-BETA-GLYCOSYLATED AROMATICS

被引：14

作者：

MABIC, S ^{[1
]}

LEPOITTEVIN, JP ^{[1
]}

机构：

[1] UNIV STRASBOURG 1,CHU,DERMATOL CLIN,CNRS,DERMATOCHIM LAB,F-67091 STRASBOURG,FRANCE

来源：

TETRAHEDRON LETTERS | 1995年 / 36卷 / 10期

关键词：

D O I：

10.1016/0040-4039(95)00050-M

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The quasi quantitative and regioselective bromination of O-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl) phenols is described. The orientating effect of the glycoside group is compared with those of other oxygenated groups and its usefulness illustrated with examples. These bromo-glycoslyated aromatics are able to react with alkenes via a Heck reaction and could be used for the synthesis of natural products.

引用

页码：1705 / 1708

页数：4

共 11 条

[1]

BRITTAIN R, 1983, CHEM FUNCTIONAL GR 1, P522

[2]

CARSON MS, 1986, NAT PROD REP, P251

[3] THE INFLUENCE OF THE METHOXYL GROUP IN AROMATIC SUBSTITUTION [J].

DELAMARE, PBD ;

VERNON, CA .

JOURNAL OF THE CHEMICAL SOCIETY, 1951, (JUL) :1764-1767

[4]

DESS D, 1981, SYNTHESIS-STUTTGART, P883

[5]

FREUDENBERG B, 1952, BER, V81, P641

[6]

HECK RF, 1982, ORG REACTIONS, P345

[7] STUDIES IN THE POLYOXYPHENOL SERIES .4. THE SYNTHESIS OF N-ETHYL-3,4-DIMETHOXYANILINE FROM GUAIACOL [J].

MOIR, RY ;

PURVES, CB .

CANADIAN JOURNAL OF RESEARCH SECTION B-CHEMICAL SCIENCES, 1948, 26 (09) :694-701

[8] Orthobromophenols and some bromonitrophenols [J].

Robertson, PW .

JOURNAL OF THE CHEMICAL SOCIETY, 1908, 93 :788-794

[9] Glucovanillin and a colour reaction for vanillin. [J].

Thorpe, WV ;

Williams, RTC .

JOURNAL OF THE CHEMICAL SOCIETY, 1937, :494-494

[10] RECENT PROGRESS IN O-GLYCOSYLATION METHODS AND ITS APPLICATION TO NATURAL-PRODUCTS SYNTHESIS [J].

TOSHIMA, K ;

TATSUTA, K .

CHEMICAL REVIEWS, 1993, 93 (04) :1503-1531

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