A NEW SYNTHESIS OF D-GLYCOSIDURONATES FROM UNPROTECTED D-URONIC ACIDS

被引：37

作者：

BERTHO, JN ^{[1
]}

FERRIERES, V ^{[1
]}

PLUSQUELLEC, D ^{[1
]}

机构：

[1] ECOLE NATL SUPER CHIM RENNES,CNRS,SYNTHESES & ACTIVAT BIOMOLEC LAB,F-35700 RENNES,FRANCE

来源：

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS | 1995年 / 13期

关键词：

D O I：

10.1039/c39950001391

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

O-Glycosidation of totally O-unprotected D-galacturonic acid 1 in THF provides alpha-pyranosides 4a when promoted with BF3.OEt(2) whereas beta-furanosides 6 beta were obtained in the presence of FeCl3; when the same reaction is performed with D-glucuronic acid 2 or ''D-glucurone'' 3, alkyl-D-glucofuranosidurono-6,3-lactones 7 are synthesized in excellent yields and high beta-selectivity.

引用

页码：1391 / 1393

页数：3

共 27 条

[1] HAWORTH MEMORIAL LECTURE - SUGAR-CATION COMPLEXES - STRUCTURE AND APPLICATIONS
ANGYAL, SJ
[J]. CHEMICAL SOCIETY REVIEWS, 1980, 9 (04) : 415 - 428
[2] SYNTHESIS OF OLIGOSACCHARIDES OF 2-AMINO-2-DEOXY SUGARS
BANOUB, J
BOULLANGER, P
LAFONT, D
[J]. CHEMICAL REVIEWS, 1992, 92 (06) : 1167 - 1195
[3] C-13 NUCLEAR MAGNETIC-RESONANCE SPECTROSCOPY OF MONOSACCHARIDES
BOCK, K
PEDERSEN, C
[J]. ADVANCES IN CARBOHYDRATE CHEMISTRY AND BIOCHEMISTRY, 1983, 41 : 27 - 66
[4] SYNTHESIS OF MORPHINE-6-GLUCURONIDE VIA A HIGHLY SELECTIVE ENZYME-CATALYZED HYDROLYSIS REACTION
BROWN, RT
CARTER, NE
SCHEINMANN, F
TURNER, NJ
[J]. TETRAHEDRON LETTERS, 1995, 36 (07) : 1117 - 1120
[5] Choay J, 1981, Ann N Y Acad Sci, V370, P644, DOI 10.1111/j.1749-6632.1981.tb29770.x
[6] SELECTIVE OXIDATION OF MONOSACCHARIDE DERIVATIVES TO URONIC-ACIDS
DAVIS, NJ
FLITSCH, SL
[J]. TETRAHEDRON LETTERS, 1993, 34 (07) : 1181 - 1184
[7] DENIJS MP, 1990, RECL TRAV CHIM PAY B, V109, P429
[8] PROPERTIES OF ACYL GLUCURONIDES - IMPLICATIONS FOR STUDIES OF THE PHARMACOKINETICS AND METABOLISM OF ACIDIC DRUGS
FAED, EM
[J]. DRUG METABOLISM REVIEWS, 1984, 15 (5-6) : 1213 - 1249
[9] THE BINDING OF CATIONS BY CHONDROITIN SULFATE
FARBER, SJ
SCHUBERT, M
SCHUSTER, N
[J]. JOURNAL OF CLINICAL INVESTIGATION, 1957, 36 (12) : 1715 - 1722
[10] A NEW SYNTHESIS OF O-GLYCOSIDES FROM TOTALLY O-UNPROTECTED GLYCOSYL DONORS
FERRIERES, V
BERTHO, JN
PLUSQUELLEC, D
[J]. TETRAHEDRON LETTERS, 1995, 36 (16) : 2749 - 2752

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