A novel reductive fragmentation reaction in thio-sugar chemistry

被引：5

作者：

Brochard, L ^{[1
]}

Lorin, C ^{[1
]}

Spiess, N ^{[1
]}

Rollin, P ^{[1
]}

机构：

[1] Univ Orleans, CNRS, Inst Chim Organ & Analyt, F-45067 Orleans 2, France

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 24期

关键词：

thiosugars; Grignard reagents; ring-cleavage; vinyl sulfides;

D O I：

10.1016/S0040-4039(98)00700-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

When reacted with Grignard reagents, azaheterocycle/thiosugar hybrids such as the benzothiazo-2-yl derivative 1 undergo a novel type of sugar ring-cleavage to build up chiral polyoxygenated vinyl sulfides with a high degree of stereocontrol. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：4267 / 4270

页数：4

共 13 条

[1] SELECTIVE DEGRADATION OF CARBOHYDRATE POLYMERS [J].

ASPINALL, GO .

PURE AND APPLIED CHEMISTRY, 1977, 49 (08) :1105-1134

[2] REACTIONS OF NITRO SUGARS .2. CONVERSION OF METHYL 6-DEOXY-6-NITRO-HEXOPYRANOSIDES INTO DEOXYNITROINOSITOLS BY ALKALINE GLYCOSIDE CLEAVAGE [J].

BAER, HH ;

RANK, W .

CANADIAN JOURNAL OF CHEMISTRY, 1965, 43 (12) :3330-&

[3] FRAGMENTATION OF 6-DEOXY-6-HALO-HEXONO-1,5-ORTHOLACTONES - A CONCERTED, NONSTEREOSPECIFIC PROCESS [J].

BERNET, B ;

VASELLA, A .

HELVETICA CHIMICA ACTA, 1984, 67 (05) :1328-1347

[4] MITSUNOBU THIOFUNCTIONALIZATION .2. AN EXPEDIENT SYNTHESIS OF AZA-HETEROCYCLE THIOSUGAR HYBRIDS [J].

BESSON, T ;

ALNEIRABEYEH, M ;

VIAUD, MC ;

ROLLIN, P .

SYNTHETIC COMMUNICATIONS, 1990, 20 (11) :1631-1639

[5] STEREOSELECTIVE SYNTHESIS OF ALCOHOLS CONTAINING (Z)-OLEFINS AND (E)-OLEFINS, DIENES, ENYNES AND STYRENES - CYCLIC BETA-HALOGENO ETHER SCISSIONS USING SAMARIUM DIIODIDE AS THE ELECTRON-TRANSFER AGENT [J].

CROMBIE, L ;

RAINBOW, LJ .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1994, (06) :673-687

[6] SYNTHESES OF ACETOGENINS OF ANNONACEAE - A NEW CLASS OF BIOACTIVE POLYKETIDES [J].

FIGADERE, B .

ACCOUNTS OF CHEMICAL RESEARCH, 1995, 28 (09) :359-365

[7] CHEMISTRY OF AND WITH HIGHLY REACTIVE METALS [J].

FURSTNER, A .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1993, 32 (02) :164-189

[8] HETEROLYTIC FRAGMENTATION . A CLASS OF ORGANIC REACTIONS [J].

GROB, CA ;

SCHIESS, PW .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1967, 6 (01) :1-&

[9]

LORIN C, UNPUB

[10] UNEXPECTED HETEROATOM-ASSISTED C-4 ALKYLATION OF A 1,3-DIOXOLANE [J].

MAROT, C ;

PHILIPP, C ;

ROLLIN, P .

TETRAHEDRON LETTERS, 1992, 33 (32) :4575-4578

← 1 2 →