SYNTHESIS OF A SERIES OF METHYL BETA-GLYCOSIDES OF (1-]6)-BETA-D-GALACTO-OLIGOSACCHARIDES HAVING ONE RESIDUE DEOXYGENATED AT POSITION-3

被引:11
作者
KOVAC, P [1 ]
EDGAR, KJ [1 ]
机构
[1] EASTMAN KODAK CO, RES LABS, EASTMAN CHEM DIV, KINGSPORT, TN 37662 USA
关键词
D O I
10.1016/0008-6215(90)84226-K
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
Methyl β-glycosides of β-(1→6)-linked d-galactobioses (13 and 16) and -galactotrioses (21, 24, and 26) containing a 3-deoxy-β-d-xylo-hexopyranosyl moiety either as one of the end units or the internal unit have been synthesized. The extension of the oligosaccharide chain was achieved, inter alia, by the use of two newly synthesized glycosyl donors derived from 3-deoxy-d-xylo-hexopyranose, namely, 2,4,6-tri-O-benzoyl-3-deoxy-α-d-xylo-hexopyranosyl chloride (8) and 2,4-di-O-benzoyl-6-O-bromoacetyl-3-deoxy-α-d-xylo-hexopyranosyl chloride (10). Glycosylation reactions were mediated by silver triflate under base-deficient conditions. © 1990.
引用
收藏
页码:79 / 93
页数:15
相关论文
共 20 条
[12]   SYNTHESIS OF SPECIFICALLY FLUORINATED METHYL BETA-GLYCOSIDES OF (1-]6)-BETA-D-GALACTO-OLIGOSACCHARIDES .5. SYNTHESIS OF METHYL O-(3-DEOXY-3-FLUORO-BETA-D-GALACTOPYRANOSYL)-(1-]6)-O-BETA-D-GALACTOPYRANOSYL-(1-]6)-3-DEOXY-3-FLUORO-BETA-D-GALACTOPYRANOSIDE AND RELATED NMR-STUDIES [J].
KOVAC, P ;
GLAUDEMANS, CPJ ;
GUO, W ;
WONG, TC .
CARBOHYDRATE RESEARCH, 1985, 140 (02) :299-311
[13]   THE REACTION OF METHYL 2,4,6-TRI-O-BENZOYL-3-O-BENZYL-BETA-D-GALACTOPYRANOSIDE WITH 1,1-DICHLOROMETHYL METHYL-ETHER [J].
KOVAC, P ;
WHITTAKER, NF ;
GLAUDEMANS, CPJ .
JOURNAL OF CARBOHYDRATE CHEMISTRY, 1985, 4 (02) :243-254
[15]   ALTERNATIVE SYNTHESES AND RELATED NMR-STUDIES OF PRECURSORS FOR INTERNAL BETA-D-GALACTOPYRANOSYL RESIDUES IN OLIGOSACCHARIDES, ALLOWING CHAIN EXTENSION AT O-4 [J].
KOVAC, P ;
TAYLOR, RB .
CARBOHYDRATE RESEARCH, 1987, 167 :153-173
[17]   IMPROVED SYNTHESIS OF THE 2-DEOXY, 3-DEOXY, AND 4-DEOXY DERIVATIVES FROM METHYL BETA-D-GALACTOPYRANOSIDE [J].
LIN, TH ;
KOVAC, P ;
GLAUDEMANS, CPJ .
CARBOHYDRATE RESEARCH, 1989, 188 :228-238
[18]   PREPARATION OF 2-DEOXY-SUGARS BY HYDROGENOLYSIS OF BENZOYLATED GLYCOPYRANOSYL BROMIDES .2. [J].
LUNDT, I ;
PEDERSEN, C .
ACTA CHEMICA SCANDINAVICA SERIES B-ORGANIC CHEMISTRY AND BIOCHEMISTRY, 1976, 30 (07) :680-684
[19]   ATTACHED PROTON TEST FOR C-13 NMR [J].
PATT, SL ;
SHOOLERY, JN .
JOURNAL OF MAGNETIC RESONANCE, 1982, 46 (03) :535-539
[20]   PHOSPHORYLATED SUGARS .2. THE SYNTHESIS OF SOME METHYL GLYCOSIDE PHOSPHATES [J].
SZABO, P ;
SZABO, L .
JOURNAL OF THE CHEMICAL SOCIETY, 1960, (OCT) :3762-3768