REACTIONS WITH AND IN ANHYDROUS HYDROGEN-FLUORIDE SYSTEMS .8. TRIETHYLAMINE TRISHYDROFLUORIDE - A CONVENIENT REAGENT FOR THE STEREOSELECTIVE SYNTHESIS OF GLYCOSYL FLUORIDES

被引：22

作者：

MIETHCHEN, R

KOLP, G

机构：

[1] Fachbereich Chemie der Universitaet, D-2500 Rostock

来源：

JOURNAL OF FLUORINE CHEMISTRY | 1993年 / 60卷 / 01期

关键词：

D O I：

10.1016/S0022-1139(00)82194-6

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Stereoselective fluorinations are effected by bromine-fluorine exchange at glycosyl bromides of the D- and L-series using triethylamine trishydrofluoride. Pyranosyl fluorides of D-xylose, L-arabinose, D-glucose, D-mannose and L-rhamnose derivatives, as well as of D-galacturonic acid esters, have been prepared. The influence of neighbouring groups in the 2-position is considered.

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页码：49 / 55

页数：7

相关论文

共 29 条

[1] CONVENIENT PREPARATION OF 2,3,4,6-TETRA-O-METHYL-ALPHA-D-GLUCOPYRANOSYL BROMIDE [J].

BATES, HA ;

SELICK, C .

JOURNAL OF CARBOHYDRATE CHEMISTRY, 1985, 4 (02) :273-275

[2] PRACTICAL SYNTHESIS OF O-BETA-D-MANNOPYRANOSYL O-ALPHA-D-MANNOPYRANOSYL AND O-BETA-D-GLUCOPYRANOSYL-(1-]4)-O-ALPHA-D-RHAMNOPYRANOSYL-(1-]3)-D-GALACTOSES [J].

BETANELI, VI ;

OVCHINNIKOV, MV ;

BACKINOWSKY, LV ;

KOCHETKOV, NK .

CARBOHYDRATE RESEARCH, 1980, 84 (02) :211-224

[3]

BINKLEY RW, 1988, MODERN CARBOHYDRATE, P53

[4] STUDY OF C-13-F-19 COUPLING-CONSTANTS IN GLYCOSYL FLUORIDES [J].

BOCK, K ;

PEDERSEN, C .

ACTA CHEMICA SCANDINAVICA SERIES B-ORGANIC CHEMISTRY AND BIOCHEMISTRY, 1975, 29 (06) :682-686

[5]

DALE J, 1978, STEREOCHEMIE KONFORM, P155

[6] DEOXY-SUGARS .5. A REINVESTIGATION OF THE GLYCAL METHOD FOR THE SYNTHESIS OF 2-DEOXY-D-RIBOSE AND 2-DEOXY-L-RIBOSE [J].

DERIAZ, RE ;

OVEREND, WG ;

STACEY, M ;

TEECE, EG ;

WIGGINS, LF .

JOURNAL OF THE CHEMICAL SOCIETY, 1949, (JUL) :1879-1883

[7]

Fischer E., 1920, BER, V53, P2362

[8] STUDIES OF SPECIFICALLY FLUORINATED CARBOHYDRATES .2. NUCLEAR MAGNETIC RESONANCE STUDIES OF PENTOPYRANOSYL FLUORIDE DERIVATIVES [J].

HALL, LD ;

MANVILLE, JF .

CANADIAN JOURNAL OF CHEMISTRY, 1969, 47 (01) :19-&

[9] STUDIES OF SPECIFICALLY FLUORINATED CARBOHYDRATES .I. NUCLEAR MAGNETIC RESONANCE STUDIES OF HEXOPYRANSOYL FLUORIDE DERIVATIVES [J].

HALL, LD ;

MANVILLE, JF ;

BHACCA, NS .

CANADIAN JOURNAL OF CHEMISTRY, 1969, 47 (01) :1-&

[10]

HOLZ J, 1992, THESIS U ROSTOCK