ELECTROORGANIC SYNTHESIS .47. OXIDATION OF PARTIALLY PROTECTED CARBOHYDRATES AT THE NICKEL-HYDROXIDE ELECTRODE

被引:27
作者
SCHAFER, HJ
SCHNEIDER, R
机构
[1] Organisch-Chemisches Institut der Universität Münster, D-4400 Münster
关键词
D O I
10.1016/S0040-4020(01)87061-7
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Primary hydroxy groups in pyranoses are oxidized in excellent yields to the corresponding carboxylic acids. In furanose 3 the yield of acid is only moderate. Secondary hydroxy groups are inert, aside from lactols. The different reactivity of secondary and primary hydroxy groups allows the chemoselective oxidation of 8 and 10.
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页码:715 / 724
页数:10
相关论文
共 42 条
[1]  
AKIYA S, 1954, J PHARM SOC JPN, V74, P360
[2]  
AKIYA S, 1944, J PHARM SOC JPN, V64, P42
[3]   Preparation of d-mannuronic acid and its derivatives [J].
Ault, RG ;
Haworth, WN ;
Hirst, EL .
JOURNAL OF THE CHEMICAL SOCIETY, 1935, :517-518
[5]   A SIMPLE AND RAPID METHOD FOR THE PERMETHYLATION OF CARBOHYDRATES [J].
CIUCANU, I ;
KEREK, F .
CARBOHYDRATE RESEARCH, 1984, 131 (02) :209-217
[6]  
COURT D, 1984, SPR M EL SOC CINC
[7]   ULTRASOUND IN ORGANIC-SYNTHESIS .8. READY PREPARATION OF SUGAR ACETALS UNDER ULTRASONIC IRRADIATION [J].
EINHORN, C ;
LUCHE, JL .
CARBOHYDRATE RESEARCH, 1986, 155 :258-261
[8]  
FELDHUES U, 1982, SYNTHESIS-STUTTGART, P145
[9]  
FELDHUES U, 1984, THESIS U MUNSTER
[10]   KINETICS AND MECHANISM OF OXIDATION OF AMINES AND ALCOHOLS AT OXIDE-COVERED NICKEL, SILVER, COPPER, AND COBALT ELECTRODES [J].
FLEISCHM.M ;
PLETCHER, D ;
KORINEK, K .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1972, (10) :1396-&