Methyl 5-deoxy-alpha and beta-D-xylofuranosides

被引:7
作者
Moravcova, J
Capkova, J
Stanek, J
Raich, I
机构
[1] Dept. of Chem. of Natural Compounds, Institute of Chemical Technology, 166 28 Prague
关键词
D O I
10.1080/07328309708005737
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
Synthesized from D-xylose, methyl 5-deoxy-alpha-D-xylofuranoside (1) and methyl 5-deoxy-beta-D-xylofuranoside (2) were obtained in overall yields of 24 and 26 %, respectively. The key step in the synthesis was the separation of an anomeric mixture on a strong anion exchanger in OH- form. NMR data and mass spectra of title compounds 1, 2, methyl 2,3-di-O-acetyl-5-deoxy-alpha-D-xylofuranoside (3), and methyl 2,3-di-O-acetyl-5-deoxy-beta-D-xylofuranoside (4) are discussed. The conformations of 1 and 2 were established from the best fit between calculated and experimental coupling constants using Karplus equation.
引用
收藏
页码:1061 / 1073
页数:13
相关论文
共 30 条
[1]   CONFORMATIONAL-ANALYSIS OF SUGAR RING IN NUCLEOSIDES AND NUCLEOTIDES - NEW DESCRIPTION USING CONCEPT OF PSEUDOROTATION [J].
ALTONA, C ;
SUNDARALINGAM, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1972, 94 (23) :8205-+
[3]  
DEJONGH DC, 1968, ADV CHEM SER, V74, P202
[4]   CONFORMATIONAL-ANALYSIS OF BETA-D-RIBO-NUCLEOSIDES, BETA-D-DEOXYRIBO-NUCLEOSIDES, BETA-D-ARABINO-NUCLEOSIDES, BETA-D-XYLO-NUCLEOSIDES, AND BETA-D-LYXO-NUCLEOSIDES FROM PROTON-PROTON COUPLING-CONSTANTS [J].
DELEEUW, FAAM ;
ALTONA, C .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1982, (03) :375-384
[5]   SYNTHESE DES BIOPTERINS UND SEINER DREI OPTISCHEN ISOMEREN [J].
GREEN, B ;
REMBOLD, H .
CHEMISCHE BERICHTE-RECUEIL, 1966, 99 (07) :2162-&
[6]   THE RELATIONSHIP BETWEEN PROTON-PROTON NMR COUPLING-CONSTANTS AND SUBSTITUENT ELECTRONEGATIVITIES .1. AN EMPIRICAL GENERALIZATION OF THE KARPLUS EQUATION [J].
HAASNOOT, CAG ;
DELEEUW, FAAM ;
ALTONA, C .
TETRAHEDRON, 1980, 36 (19) :2783-2792
[7]   REACTION OF O-BENZYLIDENE SUGARS WITH N-BROMOSUCCINIMIDE .4. NEIGHBORING-GROUP EFFECTS AND REARRANGEMENTS [J].
HANESSIAN, S ;
PLESSAS, NR .
JOURNAL OF ORGANIC CHEMISTRY, 1969, 34 (04) :1053-+
[8]   MASSENSPEKTROMETRISCHE UNTERSUCHUNGEN .7. DER EINFLUSS VON RINGGROSSE UND STEREOCHEMIE IN DEN MASSENSPEKTREN DER PERMETHYLIERTEN PENTOSEN [J].
HEYNS, K ;
SCHARMAN.H .
TETRAHEDRON, 1965, 21 (03) :507-&
[9]  
HIROYSHI K, 1963, AGR BIOL CHEM TOKYO, V27, P689
[10]   ACYLOXY NEIGHBORING-GROUP PARTICIPATION IN ACID-CATALYZED CLEAVAGE OF METHYL 2,3-ANHYDRO-BETA-D-RIBOFURANOSIDE [J].
HOLLENBERG, DH ;
WATANABE, KA ;
FOX, JJ .
CARBOHYDRATE RESEARCH, 1975, 42 (02) :241-249