Synthesis of novel mannose-based crown ethers

被引：0

作者：

Rathjens, A ^{[1
]}

Thiem, J ^{[1
]}

机构：

[1] Univ Hamburg, Inst Organ Chem, D-20146 Hamburg, Germany

来源：

POLISH JOURNAL OF CHEMISTRY | 2005年 / 79卷 / 02期

关键词：

carbohydrates; disaccharide mimetics; macrocyles; Richman-Atkins cyclization;

D O I：

暂无

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A novel class of chiral crown ether analogues incorporating carbohydrate subunits can be easily prepared from methyl alpha-D-mannopyranoside. By a short reaction sequence involving either alkylations using a dibutylstannane intermediate or by phase transfer catalyzed etherification well defined disaccharide mimetics were obtained, which are suitable starting materials in Richman-Atkins cyclizations. The combination of several various reaction partners led to structurally interesting ring systems differing in ring size, number of carbon and hetero atoms (20-40) as well as kind of sugar subunits.

引用

页码：211 / 222

页数：12

共 46 条

[1] CHIRAL MACROCYCLIC-COMPOUNDS FROM LACTOSE DERIVATIVES [J].

ALONSOLOPEZ, M ;

BERNABE, M ;

FERNANDEZMAYORALAS, A ;

JIMENEZBARBERO, J ;

MARTINLOMAS, M ;

PENADES, S .

CARBOHYDRATE RESEARCH, 1986, 150 (01) :103-109

[2] ASYMMETRIC MICHAEL REACTION USING MACROCYCLIC LACTOSE DERIVATIVES AS CHIRAL CATALYSTS [J].

ALONSOLOPEZ, M ;

MARTINLOMAS, M ;

PENADES, S .

TETRAHEDRON LETTERS, 1986, 27 (30) :3551-3554

[3]

BAKO P, 1981, LIEBIGS ANN CHEM, P1163

[4] SYNTHESIS OF 4-O-BETA-D-MANNOPYRANOSYL-L-RHAMNOPYRANOSE [J].

BEBAULT, GM ;

DUTTON, GGS .

CARBOHYDRATE RESEARCH, 1974, 37 (02) :309-319

[5] HYDROGENOLYSIS OF CARBOHYDRATE ACETALS KETALS AND CYCLIC ORTHOESTERS WITH LITHIUM ALUMINIUM YDRIDE - ALUMINIUM TRICHLORIDE [J].

BHATTACH.SS ;

GORIN, PAJ .

CANADIAN JOURNAL OF CHEMISTRY, 1969, 47 (07) :1195-&

[6] CHEMISTRY OF SYNTHETIC RECEPTORS AND FUNCTIONAL-GROUP ARRAYS .6. SYNTHETIC RECEPTORS - 3,6-ANHYDRO-7-BENZENESULFONAMIDO-1,7-DIDEOXY-4,5-O-ISOPROPYLIDENE-D-ALTRO-HEPT-1-YNITOL - A USEFUL COMPONENT FOR THE PREPARATION OF CHIRAL WATER-SOLUBLE CYCLOPHANES BASED ON CARBOHYDRATE PRECURSORS [J].

BUKOWNIK, RR ;

WILCOX, CS .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (03) :463-471

[7] GLYCOPHANES, CYCLODEXTRIN CYCLOPHANE HYBRID RECEPTORS FOR APOLAR BINDING IN AQUEOUS-SOLUTIONS - A STEREOSELECTIVE CARBOHYDRATE CARBOHYDRATE INTERACTION IN WATER [J].

COTERON, JM ;

VICENT, C ;

BOSSO, C ;

PENADES, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (22) :10066-10076

[8] DESIGN OF COMPLEXES BETWEEN SYNTHETIC HOSTS AND ORGANIC GUESTS [J].

CRAM, DJ ;

CRAM, JM .

ACCOUNTS OF CHEMICAL RESEARCH, 1978, 11 (01) :8-14

[9] CHIRAL RECOGNITION IN COMPLEXATION OF GUESTS BY DESIGNED HOST MOLECULES [J].

CRAM, DJ ;

HELGESON, RC ;

SOUSA, LR ;

TIMKO, JM ;

NEWCOMB, M ;

MOREAU, P ;

DEJONG, F ;

GOKEL, GW ;

HOFFMAN, DH ;

DOMEIER, LA ;

PEACOCK, SC ;

MADAN, K ;

KAPLAN, L .

PURE AND APPLIED CHEMISTRY, 1975, 43 (3-4) :327-349

[10]

Dehmlow E. V., 1993, Phase Transfer Catalysis

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