Synthesis of uronic acid derivatives from 1,2;3,4-di-O-isopropylidene-α-D-galacto-hexodialdo-pyranose and aldulosonic acid derivatives from 2,3;4,5-di-O-isopropylidene-β-D-arabino-hexos-2-ulopyranose

被引:4
作者
González, Z [1 ]
González, A [1 ]
机构
[1] Univ Publ Navarra, Dept Quim Aplicada, E-31006 Pamplona, Spain
关键词
uronic acids; ketoaldonic acids;
D O I
10.1016/S0008-6215(99)00070-1
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
A facile method for the formation of uronic and aldulosonic acids derivatives is described involving reaction of lithium dianions of carboxylic acids with aldehydo-sugar derivatives. Acetic, propanoic, phenylacetic, 3,3-dimethylacrylic, crotonic, and sorbic acids were the acids used for the preparation of the lithium dianions, and galactose and fructose were used for preparation of the aldehydo derivatives. (C) 1999 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:217 / 222
页数:6
相关论文
共 12 条
[1]  
[Anonymous], CARBOHYDRATES
[2]  
GENTILE B, 1979, THESIS U GENEVE
[3]  
GONZALEZ Z, 1997, THESIS U PUBLICA NAV
[4]  
Gottschalk A., 1960, CHEM BIOL SIALIC ACI
[5]  
HANZAWA Y, 1991, CHEM PHARM BULL, V39, P2459
[6]   A GENERAL-SYNTHESIS OF METHYL ALDULOSONATES USING TRIS (METHYLTHIO) METHYL LITHIUM AS THE ESTER ANION EQUIVALENT [J].
HENGEVELD, JE ;
GRIEF, V ;
TADANIER, J ;
LEE, CM ;
RILEY, D ;
LARTEY, PA .
TETRAHEDRON LETTERS, 1984, 25 (37) :4075-4078
[7]  
HOPPE I, 1983, LIEBIGS ANN CHEM, P372
[8]   ALPHA ANIONS OF CARBOXYLIC-ACIDS .2. FORMATION AND ALKYLATION OF ALPHA-METALATED ALIPHATIC ACIDS [J].
PFEFFER, PE ;
SILBERT, LS ;
CHIRINKO, JM .
JOURNAL OF ORGANIC CHEMISTRY, 1972, 37 (03) :451-&
[9]   INVERTED STEREOSELECTIVITY IN GRIGNARD ADDITIONS TO CHIRAL ALDEHYDES BY USE OF POLYETHERS [J].
REITSTOEN, B ;
KILAAS, L ;
ANTHONSEN, T .
ACTA CHEMICA SCANDINAVICA SERIES B-ORGANIC CHEMISTRY AND BIOCHEMISTRY, 1986, 40 (06) :440-443
[10]  
STRAIN SM, 1983, J BIOL CHEM, V258, P2906