The Wittig-cyclization procedure:: acid promoted intramolecular formation of 3-C-branched-chain 3,6-anhydro furano sugars via 2′-oxopropylene derivatives

被引：7

作者：

Ay, Kadir

Cetin, Fatma

Yuceer, Levent ^{[1
]}

机构：

[1] Celal Bayar Univ, Fac Art & Sci, Dept Chem, TR-45040 Manisa, Turkey

[2] Ege Univ, Fac Sci, Dept Chem, TR-35100 Izmir, Turkey

来源：

CARBOHYDRATE RESEARCH | 2007年 / 342卷 / 08期

关键词：

branched-chain sugars; anhydrosugars; Wittig-cyclization; intramolecular ring-closure; C-GLYCOSYL COMPOUNDS; STEREOSELECTIVITY; CHEMISTRY; LACTONES;

D O I：

10.1016/j.carres.2007.02.021

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

Some olefinic Wittig products, 3-deoxy-5,6-O-isopropylidene-3-C-(2'-oxopropylene)-1,2-O-alkylidene hexofuranose derivatives were converted to the branched-chain 3,6-anhydro-3-C-(2'-oxopropyl) derivatives on treatment with ion exchange resin Amberlite 120 (H+) in methanol-water at room temperature. Hydrolysis of 5,6-isopropylidene groups and intramolecular ringclosures took place in one pot reactions. (c) 2007 Elsevier Ltd. All rights reserved.

引用

收藏

页码：1091 / 1095

页数：5

相关论文

共 25 条

[1] Wittig approach to carbohydrate-derived vinyl sulfides, new substrates for regiocontrolled ring-closure reactions [J].

Aucagne, V ;

Tatibouët, A ;

Rollin, P .

TETRAHEDRON, 2004, 60 (08) :1817-1826

[2] STEREOCONTROLLED ROUTES TO FUNCTIONALIZED C-GLYCOPYRANOSIDES [J].

DAWE, RD ;

FRASERREID, B .

JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (03) :522-528

[3] A NEW ROUTE TO C-GLYCOSYL COMPOUNDS - WITTIG-TYPE REACTION PROMOTED BY ZINC [J].

DHEILLY, L ;

FRECHOU, C ;

BEAUPERE, D ;

UZAN, R ;

DEMAILLY, G .

CARBOHYDRATE RESEARCH, 1992, 224 :301-306

[4] TRICHLOROETHYLIDENE DERIVATES OF D-GLUCOSE [J].

FORSEN, S ;

LINDBERG, B ;

SILVANDE.BG .

ACTA CHEMICA SCANDINAVICA, 1965, 19 (02) :359-&

[5] STEREOSELECTIVITY IN THE ELECTROPHILE-MEDIATED CYCLIZATION OF 2,3,5-TRI-O-BENZYL-1,2-DIDEOXY-D-ARABINO-HEX-1-ENITOL - A STEREOCONTROLLED SYNTHESIS OF 1-AMINO-2,5-ANHYDRO-3,4,6-TRI-O-BENZYL-1-DEOXY-D-GLUCITOL [J].

FREEMAN, F ;

ROBARGE, KD .

CARBOHYDRATE RESEARCH, 1987, 171 :1-11

[6] DIASTEREOSELECTIVE SYNTHESIS OF FUNCTIONALIZED C-ALPHA-GLYCOSYL DERIVATIVES AND C-BETA-GLYCOSYL DERIVATIVES OF 2-ACETAMIDO-2-DEOXY-D-GLUCOSE [J].

GIANNIS, A ;

SANDHOFF, K .

CARBOHYDRATE RESEARCH, 1987, 171 :201-210

[7] STEREOSELECTIVITY IN THE FORMATION OF UNSATURATED WITTIG PRODUCTS AND STEREOSPECIFICITY IN THEIR ELECTROPHILE INDUCED CYCLIZATION TO C-GLYCOSIDES [J].

HERRERA, FJL ;

GONZALEZ, MSP ;

SAMPEDRO, MN ;

ACIEGO, RMD .

TETRAHEDRON, 1989, 45 (01) :269-276

[8] MOLECULAR SIEVE-ASSISTED OXIDATIONS - NEW METHODS FOR CARBOHYDRATE DERIVATIVE OXIDATIONS [J].

HERSCOVICI, J ;

ANTONAKIS, K .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1980, (12) :561-562

[9]

ISHIDO K, 1988, J PHARM SOC JPN, V108, P71

[10] Wittig olefination of partially protected sugar lactones: A direct entry to dioxabicyclic and trioxatricyclic systems [J].

Lakhrissi, M ;

Taillefumier, C ;

Chaouch, A ;

Didierjean, C ;

Aubry, A ;

Chapleur, Y .

TETRAHEDRON LETTERS, 1998, 39 (36) :6457-6460