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
ASPINALL, GO
[J]. 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
BAER, HH
RANK, W
[J]. CANADIAN JOURNAL OF CHEMISTRY, 1965, 43 (12): : 3330 - &
[3] FRAGMENTATION OF 6-DEOXY-6-HALO-HEXONO-1,5-ORTHOLACTONES - A CONCERTED, NONSTEREOSPECIFIC PROCESS
BERNET, B
VASELLA, A
[J]. HELVETICA CHIMICA ACTA, 1984, 67 (05) : 1328 - 1347
[4] MITSUNOBU THIOFUNCTIONALIZATION .2. AN EXPEDIENT SYNTHESIS OF AZA-HETEROCYCLE THIOSUGAR HYBRIDS
BESSON, T
ALNEIRABEYEH, M
VIAUD, MC
ROLLIN, P
[J]. 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
CROMBIE, L
RAINBOW, LJ
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1994, (06): : 673 - 687
[6] SYNTHESES OF ACETOGENINS OF ANNONACEAE - A NEW CLASS OF BIOACTIVE POLYKETIDES
FIGADERE, B
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 1995, 28 (09) : 359 - 365
[7] CHEMISTRY OF AND WITH HIGHLY REACTIVE METALS
FURSTNER, A
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1993, 32 (02) : 164 - 189
[8] HETEROLYTIC FRAGMENTATION . A CLASS OF ORGANIC REACTIONS
GROB, CA
SCHIESS, PW
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1967, 6 (01) : 1 - &
[9] LORIN C, UNPUB
[10] UNEXPECTED HETEROATOM-ASSISTED C-4 ALKYLATION OF A 1,3-DIOXOLANE
MAROT, C
PHILIPP, C
ROLLIN, P
[J]. TETRAHEDRON LETTERS, 1992, 33 (32) : 4575 - 4578

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