SYNTHESIS OF OPTICALLY-ACTIVE GLYCERIC ACID-DERIVATIVES FROM ASCORBIC ACIDS

被引:10
作者
CARLSEN, PHJ
MISUND, K
ROE, J
机构
[1] BORREGARD FINE CHEM,RES & DEV,N-1701 SARPSBORG,NORWAY
[2] WEIDERS FARMASOYTISKE AS,N-0133 OSLO,NORWAY
来源
ACTA CHEMICA SCANDINAVICA | 1995年 / 49卷 / 04期
关键词
D O I
10.3891/acta.chem.scand.49-0297
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
The synthesis of acetals and ketals of L-ascorbic acid and D-isoascorbic acid has been studied. A convenient and inexpensive method involving reflux in acetone in the presence of an acidic ion-exchange resin was developed. In a perruthenate-catalyzed oxidative degradation reaction using sodium hypochlorite as the stoichiometric oxidant at pH 8.0, acetals or ketals of L-ascorbic acid were converted in high yields into the corresponding acetals or ketals of (S)-glyceric acid as their sodium salts. D-Isoascorbic acid similarly gave the (R)-glyceric acid derivatives.
引用
收藏
页码:297 / 300
页数:4
相关论文
共 39 条
[21]   (R)-2,3-O-ISOPROPYLIDENEGLYCERALDEHYDE AND (S)-2,3-O-ISOPROPYLIDENEGLYCERALDEHYDE IN STEREOSELECTIVE ORGANIC-SYNTHESIS [J].
JURCZAK, J ;
PIKUL, S ;
BAUER, T .
TETRAHEDRON, 1986, 42 (02) :447-488
[22]  
KANDA P, 1981, J LIPID RES, V22, P879
[23]   THE OXIDATION OF ALCOHOLS BY SODIUM RUTHENATE [J].
LEE, DG ;
CONGSON, LN ;
SPITZER, UA ;
OLSON, ME .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1984, 62 (09) :1835-1839
[24]   CHIRAL ALPHA-HYDROXY-AND ALPHA,BETA-DIHYDROXY-ALDEHYDES FROM D-ISOASCORBIC AND L-ASCORBIC ACIDS - USEFUL PRECURSORS FOR THE SYNTHESIS OF FATTY-ACID METABOLITES [J].
LEMERRER, Y ;
GRAVIERPELLETIER, C ;
DUMAS, J ;
DEPEZAY, JC .
TETRAHEDRON LETTERS, 1990, 31 (07) :1003-1006
[25]  
LOHRAY BB, 1989, TETRAHEDRON LETT, V30, P2041
[26]   SYNTHESIS OF CHIRAL GLYCERIDES STARTING FROM D-SERINE AND L-SERINE [J].
LOK, CM ;
WARD, JP ;
VANDORP, DA .
CHEMISTRY AND PHYSICS OF LIPIDS, 1976, 16 (02) :115-122
[27]  
MAI KH, 1836, Patent No. 213
[28]  
PFENNINGER A, 1986, SYNTHESIS-STUTTGART, P89
[29]  
POTIE M, 1989, TETRAHEDRON LETT, V30, P5319
[30]   Transport of salts from acetonesed sugar acid in their methyl esters [J].
Reichstein, T ;
Pedolin, A ;
Grussner, A .
HELVETICA CHIMICA ACTA, 1935, 18 :598-601