Palladium(0)-mediated synthesis of acetylated unsaturated 1,4-disaccharides

被引：13

作者：

Frappa, I

Kryczka, B

Lhoste, P

Porwanski, S

Sinou, D

Zawisza, A

机构：

[1] Univ Lyon 1, CPE Lyon, CNRS, Lab Synthese Asymetr, F-69622 Villeurbanne, France

[2] Univ Lodz, Inst Organ & Appl Chem, PL-90136 Lodz, Poland

来源：

JOURNAL OF CARBOHYDRATE CHEMISTRY | 1998年 / 17卷 / 07期

关键词：

D O I：

10.1080/07328309808001888

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：

Alkylation of ethyl 6-O-tert-butyldiphenylsilyl-4-O-methoxycarbonyl-2,3-dideoxy alpha-D-erythro-hex-2-enopyranoside (1) with various peracetylated 1-hydroxy sugars in the presence of a catalytic amount of palladium(0) gave the corresponding unsaturated 1,4-disaccharides and trisaccharides. In all cases the reaction is regio- and stereospecific according to the unsaturated moiety, alkylation occuring only at C-4 of the unsaturated carbohydrate, with overall retention of configuration.

引用

收藏

页码：1117 / 1130

页数：14

相关论文

共 46 条

[1] SYNTHESIS OF OLIGOSACCHARIDES OF 2-AMINO-2-DEOXY SUGARS [J].

BANOUB, J ;

BOULLANGER, P ;

LAFONT, D .

CHEMICAL REVIEWS, 1992, 92 (06) :1167-1195

[2]

BOCHKOV F, 1979, CHEM O GLYCOSIDIC BO

[3] STUDY OF CH-13 COUPLING-CONSTANTS IN PENTOPYRANOSES AND SOME OF THEIR DERIVATIVES [J].

BOCK, K ;

PEDERSEN, C .

ACTA CHEMICA SCANDINAVICA SERIES B-ORGANIC CHEMISTRY AND BIOCHEMISTRY, 1975, B 29 (02) :258-264

[4]

BREITMAI.E, 1972, CHIMIA, V26, P136

[5] TOTALLY SYNTHETIC ROUTES TO THE HIGHER MONOSACCHARIDES [J].

DANISHEFSKY, SJ ;

DENINNO, MP .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1987, 26 (01) :15-23

[6] SYNTHESIS OF PYRAZOMYCINS [J].

DEBERNARDO, S ;

WEIGELE, M .

JOURNAL OF ORGANIC CHEMISTRY, 1976, 41 (02) :287-290

[7] UNSATURATED CARBOHYDRATES .9. SYNTHESIS OF 2,3-DIDEOXY-ALPHA-D-ERYTHRO-HEX-2-ENOPYRANOSIDES FROM TRI-O-ACETYL-D-GLUCAL [J].

FERRIER, RJ ;

PRASAD, N .

JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1969, (04) :570-&

[8] A NEW SYNTHESIS OF O-GLYCOSIDES FROM TOTALLY O-UNPROTECTED GLYCOSYL DONORS [J].

FERRIERES, V ;

BERTHO, JN ;

PLUSQUELLEC, D .

TETRAHEDRON LETTERS, 1995, 36 (16) :2749-2752

[9] Stereoselective palladium(0)-mediated synthesis of unsaturated 1,4-disaccharides [J].

Frappa, I ;

Kryczka, B ;

Lhoste, P ;

Porwanski, S ;

Sinou, D .

JOURNAL OF CARBOHYDRATE CHEMISTRY, 1997, 16 (06) :891-910

[10] A ROUTE TO UNSATURATED SPIROKETALS FROM PHENYLTHIO HEX-2-ENOPYRANOSIDES VIA SEQUENTIAL ALKYLATION, ALLYLIC REARRANGEMENT AND INTRAMOLECULAR GLYCOSIDATION [J].

GOMEZ, AM ;

VALVERDE, S ;

FRASERREID, B .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1991, (17) :1207-1208

← 1 2 3 4 5 →