Gas chromatographic investigation of the boron trifluoride etherate-induced formation and anomerization of glucopyranosides

被引：10

作者：

Ellervik, U ^{[1
]}

Jansson, K ^{[1
]}

Magnusson, G ^{[1
]}

机构：

[1] Univ Lund, Ctr Chem & Chem Engn, S-22100 Lund, Sweden

来源：

JOURNAL OF CARBOHYDRATE CHEMISTRY | 1998年 / 17卷 / 4-5期

关键词：

D O I：

10.1080/07328309808002351

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：

Boron trifluoride etherate-induced glucosylation of methanol, 1-propanol, 2-propanol, 2-bromoethanol, and 3-bromo-2-(bromomethyl)propan-1-ol, using 1,2,3,4,6-penta-O-acetyl-beta-D-glucopyranose as donor, gave the corresponding beta-glucopyranosides. The alpha-glucosides and 1,2,3,4,6-penta-O-acetyl-alpha-D-glucopyranose were formed as byproducts in varying amounts, according to GLC analysis. The propensity of the different glucopyranosides to anomerize was determined in separate experiments.

引用

页码：777 / 784

页数：8

共 11 条

[1] 3-BROMO-2-BROMOMETHYLPROPYL GLYCOSIDES IN THE PREPARATION OF DOUBLE-CHAIN BIS-SULFIDE NEO-GLYCOLIPIDS [J].

ANSARI, AA ;

FREJD, T ;

MAGNUSSON, G .

CARBOHYDRATE RESEARCH, 1987, 161 (02) :225-233

[2] 2-BROMOETHYL GLYCOSIDES .7. SYNTHESIS OF SPACER-ARM, LIPID, AND ETHYL GLYCOSIDES OF THE TERMINAL TRISACCHARIDE [ALPHA-D-GAL-(1-]4)-BETA-D-GAL-(1-]4)-BETA-D-GLCNAC] PORTION OF THE BLOOD-GROUP-P1 ANTIGEN - PREPARATION OF NEOGLYCOPROTEINS [J].

DAHMEN, J ;

FREJD, T ;

MAGNUSSON, G ;

NOORI, G ;

CARLSTROM, AS .

CARBOHYDRATE RESEARCH, 1984, 129 (JUL) :63-71

[3] 2-BROMOETHYL GLYCOSIDES - SYNTHESIS AND CHARACTERIZATION [J].

DAHMEN, J ;

FREJD, T ;

GRONBERG, G ;

LAVE, T ;

MAGNUSSON, G ;

NOORI, G .

CARBOHYDRATE RESEARCH, 1983, 116 (02) :303-307

[4] NOTIZ UBER DIE SYNTHESE ZWEIER ALPHA-D-GLUCOSIDE [J].

HELFERICH, B ;

MITAL, HC .

CHEMISCHE BERICHTE-RECUEIL, 1960, 93 (04) :1010-1011

[5] 2-(TRIMETHYLSILYL)ETHYL GLYCOSIDES .3. SYNTHESIS, ANOMERIC DEBLOCKING, AND TRANSFORMATION INTO 1,2-TRANS 1-O-ACYL SUGARS [J].

JANSSON, K ;

AHLFORS, S ;

FREJD, T ;

KIHLBERG, J ;

MAGNUSSON, G ;

DAHMEN, J ;

NOORI, G ;

STENVALL, K .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (24) :5629-5647

[6] ACTION OF STRONG ACIDS ON ACETYLATED GLYCOSIDES .1. TRANSFORMATION OF SOME ALIPHATIC TETRAACETYL-BETA-GLUCOSIDES TO THE ALPHA-FORM [J].

LINDBERG, B .

ACTA CHEMICA SCANDINAVICA, 1948, 2 (5-6) :426-429

[7] SYNTHESES AND PROPERTIES OF SOME ACETYLATED ALKYL GLUCOSIDES [J].

LINDBERG, B .

ACTA CHEMICA SCANDINAVICA, 1949, 3 (02) :151-156

[8] One-step glycosylation and selective deprotection of peracetylated monosaccharides for facile syntheses of allyl glycosides with a free C-2 hydroxyl group [J].

Liu, MZ ;

Fan, HN ;

Guo, ZW ;

Hui, YZ .

CARBOHYDRATE RESEARCH, 1996, 290 (02) :233-237

[9]

MAGNUSSON G, 1981, Acta Chemica Scandinavica Series B Organic Chemistry and Biochemistry, V35, P213, DOI 10.3891/acta.chem.scand.35b-0213

[10]

MAGNUSSON G, 1990, J ORG CHEM, V55, P3933

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