New synthesis of 2,6-anhydro-β-D-fructofuranoses, pivotal [2.2.1] bicyclic acetals for the conversion of D-fructose into 2,2,5-trisubstituted tetrahydrofurans

被引：9

作者：

Goursaud, F ^{[1
]}

Peyrane, F ^{[1
]}

Veyrières, A ^{[1
]}

机构：

[1] Ecole Natl Super Chim Rennes, CNRS, UMR 6052, Lab Synth & Activat Biomol, F-35700 Rennes, France

来源：

TETRAHEDRON | 2002年 / 58卷 / 18期

关键词：

allylation; bicyclic heterocyclic compounds; thioglycosides; tin and compounds;

D O I：

10.1016/S0040-4020(02)00233-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

2,6-Anhydro-beta-D-fructofuranose derivatives were prepared by a novel tin-promoted 2,5-cyclisation of phenyl 2-thio-beta-D-fructopyranosides. They were regioselectively opened by allyltrimethylsilane in the presence of catalytic Sc(OTf)(3) to give 2,2,5-tri substituted tetrahydrofurans in high yields and major alpha-stereoselectivity. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

收藏

页码：3629 / 3637

页数：9

相关论文

共 31 条

[1] Scandium trifluoromethanesulfonate, a novel catalyst for the addition of allyltrimethylsilane to aldehydes. [J].

Aggarwal, VK ;

Vennall, GP .

TETRAHEDRON LETTERS, 1996, 37 (21) :3745-3746

[2] BONDING STUDIES OF COMPOUNDS OF BORON AND GROUP IV ELEMENTS .8. HEATS OF HYDROLYSIS AND BOND ENERGIES FOR SOME TRIMETHYLMETALYL DERIVATIVES ME3M-X(M= SI, GE, AND SN) [J].

BALDWIN, JC ;

LAPPERT, MF ;

PEDLEY, JB ;

POLAND, JS .

JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1972, (18) :1943-&

[3] AN EFFICIENT SYNTHESIS OF ANHYDROALDITOLS AND ALLYL C-GLYCOSIDES [J].

BENNEK, JA ;

GRAY, GR .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (05) :892-897

[4] Tin-mediated equilibration of the benzoate esters of methyl 4,6-O-benzylidene-α-D-glucopyranoside [J].

Bredenkamp, MW ;

Spies, HSC .

TETRAHEDRON LETTERS, 2000, 41 (04) :543-546

[5] THE PREPARATION AND REACTIONS OF A NEW GLYCOSIDE - 2'-CHLOROETHYL-BETA-D-FRUCTOPYRANOSIDE [J].

CHAN, JYC ;

CHEONG, PPL ;

HOUGH, L ;

RICHARDSON, AC .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1985, (07) :1447-1455

[6] Template-directed intramolecular C-glycosidation.: Cation-mediated synthesis of ketooxetanes from thioglycosides [J].

Craig, D ;

Munasinghe, VRN ;

Tierney, JP ;

White, AJP ;

Williams, DJ ;

Williamson, C .

TETRAHEDRON, 1999, 55 (52) :15025-15044

[7] SYNTHESIS OF RIBOSYL AND ARABINOSYL CYANIDES BY REACTION OF 1-O-ACYL SUGARS WITH TRIMETHYLSILYL CYANIDE [J].

DELASHERAS, FG ;

FERNANDEZRESA, P .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1982, (04) :903-907

[8]

Deslongchamps P., 1983, Stereoelectronic Effects in Organic Chemistry

[9] SYNTHESIS OF 1,2-TRANS-RELATED 1-THIOGLYCOSIDE ESTERS [J].

FERRIER, RJ ;

FURNEAUX, RH .

CARBOHYDRATE RESEARCH, 1976, 52 (DEC) :63-68

[10] HYDROGENOLYSIS OF CARBOHYDRATES .9. FORMATION OF 2,6-ANHYDRO-BETA-D-FRUCTOFURANOSE AND ETHYL ALPHA-FRUCTOFURANOSIDE AND BETA-D-FRUCTOFURANOSIDE FROM SUCROSE [J].

GOLDSCHMID, HR ;

PERLIN, AS .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1960, 38 (11) :2178-2186

← 1 2 3 4 →