Synthesis of L-glucose from D-gulono-1,4-lactone

被引:14
作者
Hajkó, J
Lipták, A
Pozsgay, V
机构
[1] Hungarian Acad Sci, Res Grp Carbohydrates, H-4010 Debrecen, Hungary
[2] NICHHD, NIH, Bethesda, MD 20892 USA
基金
匈牙利科学研究基金会;
关键词
monosaccharide; L-glucose; unnatural carbohydrate;
D O I
10.1016/S0008-6215(99)00192-5
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
An efficient method for the synthesis of L-glucose from D-gulono-1,4-lactone via 1,2,3,4,5-penta-O-benzyl/acetyl/benzoyl-D-gulitol is described in 34-53% overall yield. (C) 1999 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:116 / 120
页数:5
相关论文
共 33 条
[1]   A SHORT ENZYMATIC-SYNTHESIS OF L-GLUCOSE FROM DIHYDROXYACETONE PHOSPHATE AND L-GLYCERALDEHYDE [J].
ALAJARIN, R ;
GARCIAJUNCEDA, E ;
WONG, CH .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (13) :4294-4295
[2]   DIMETHYL SULFOXIDE-ACID ANHYDRIDE MIXTURES . NEW REAGENTS FOR OXIDATION OF ALCOHOLS [J].
ALBRIGHT, JD ;
GOLDMAN, L .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1965, 87 (18) :4214-+
[3]   Conformational stabilization of the altruronic acid residue in the O-specific polysaccharide of Shigella sonnei Plesiomonas shigelloides [J].
Batta, G ;
Lipták, A ;
Schneerson, R ;
Pozsgay, V .
CARBOHYDRATE RESEARCH, 1997, 305 (01) :93-99
[4]   INTERACTIVITY OF CHIRAL CATALYSTS AND CHIRAL AUXILIARIES IN THE CYCLOADDITION OF ACTIVATED DIENES WITH ALDEHYDES - A SYNTHESIS OF L-GLUCOSE [J].
BEDNARSKI, M ;
DANISHEFSKY, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (22) :7060-7067
[5]   RAPID AND SELECTIVE DETRITYLATION OF PRIMARY ALCOHOLS USING FORMIC-ACID [J].
BESSODES, M ;
KOMIOTIS, D ;
ANTONAKIS, K .
TETRAHEDRON LETTERS, 1986, 27 (05) :579-580
[6]  
BILIK V, 1972, CHEM ZVESTI, V26, P187
[7]  
Bols M., 1996, CARBOHYDRATE BUILDIN
[8]  
CREE GM, 1969, CAN J CHEMISTRY, V47, P511
[9]   A USEFUL 12-I-5 TRIACETOXYPERIODINANE (THE DESS-MARTIN PERIODINANE) FOR THE SELECTIVE OXIDATION OF PRIMARY OR SECONDARY ALCOHOLS AND A VARIETY OF RELATED 12-I-5 SPECIES [J].
DESS, DB ;
MARTIN, JC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (19) :7277-7287
[10]   READILY ACCESSIBLE 12-I-5 OXIDANT FOR THE CONVERSION OF PRIMARY AND SECONDARY ALCOHOLS TO ALDEHYDES AND KETONES [J].
DESS, DB ;
MARTIN, JC .
JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (22) :4155-4156