NOVEL-APPROACH TO THE SYNTHESIS OF SUGAR SULFONES VIA TRANS-SULFONYLATION OF A UNIQUE HETEROARYL PRECURSOR

被引：8

作者：

LORIN, C ^{[1
]}

MAROT, C ^{[1
]}

GARDON, V ^{[1
]}

ROLLIN, P ^{[1
]}

机构：

[1] UNIV ORLEANS,CNRS,CHIM BIOORGAN & ANALYT LAB,F-45067 ORLEANS 02,FRANCE

来源：

TETRAHEDRON LETTERS | 1995年 / 36卷 / 25期

关键词：

THIOSUGARS; CHIRAL SULFONES; HETEROARYLSULFONES; IPSO SUBSTITUTION;

D O I：

10.1016/0040-4039(95)00811-P

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A wide range of sugar-derived sulfones were synthesized from a unique ''mother'' heteroarylsulfone 3 through a simple trans-sulfonylation process based on an ipso-substitution l alkylation sequence.

引用

页码：4437 / 4438

页数：2

共 13 条

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

ASPINALL, GO .

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

[2] A DIRECT SYNTHESIS OF OLEFINS BY REACTION OF CARBONYL-COMPOUNDS WITH LITHIO DERIVATIVES OF 2-[ALKYL-SULFONYL OR (2'-ALKENYL)-SULFONYL OR BENZYL-SULFONYL]-BENZOTHIAZOLES [J].

BAUDIN, JB ;

HAREAU, G ;

JULIA, SA ;

RUEL, O .

TETRAHEDRON LETTERS, 1991, 32 (09) :1175-1178

[3] PREPARATION AND REDUCTIVE LITHIATION OF 2-DEOXY-D-GLUCOPYRANOSYL PHENYLSULFONES - A HIGHLY STEREOSELECTIVE ROUTE TO C-GLYCOSIDES [J].

BEAU, JM ;

SINAY, P .

TETRAHEDRON LETTERS, 1985, 26 (50) :6185-6188

[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]

CHENEDE A, 1994, SYNLETT, P420

[6]

DEPOUILLY P, 1993, B SOC CHIM FR, V130, P256

[7]

FERNANDEZMAYORA.A, 1989, CARBOHYD RES, V188, P81

[8] SYNTHESIS OF NEW GLUCOSIDE SURFACTANTS USING HALOGENATED SUGARS - THIOETHER AND SULFONE DERIVATIVES OF METHYL ALPHA-D-GLUCOSIDE AND METHYL ALPHA-D-MANNOSIDE [J].

LEONRUAUD, P ;

PLUSQUELLEC, D .

TETRAHEDRON, 1991, 47 (28) :5185-5192

[9] NOVEL-APPROACH TO THE SYNTHESIS OF CHIRAL OXACYCLES VIA RING-CLOSURE OF SUGAR-DERIVED VINYL SULFONES [J].

MAROT, C ;

ROLLIN, P .

TETRAHEDRON LETTERS, 1994, 35 (45) :8377-8380

[10] SAMARIUM IODIDE INDUCED INTRAMOLECULAR C-GLYCOSIDE FORMATION - EFFICIENT RADICAL FORMATION IN THE ABSENCE OF AN ADDITIVE [J].

MAZEAS, D ;

SKRYDSTRUP, T ;

DOUMEIX, O ;

BEAU, JM .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1994, 33 (13) :1383-1386

← 1 2 →