Direct oxidative amidation of aldoses by iodine in ammonia water

被引:9
作者
Chen, MY
Hsu, JL
Shie, JJ
Fang, JM [1 ]
机构
[1] Taipei Nursing Coll, Dept Gen Educ, Taipei, Taiwan
[2] Natl Taiwan Univ, Dept Chem, Taipei 106, Taiwan
关键词
aldoses; amides; iodine; ammonia;
D O I
10.1002/jccs.200300018
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Aldopentoses, aldohexoses and the benzylated derivatives reacted with iodine in ammonia water at room temperature to give their corresponding saccharide amides in high yields. The reactions proceeded with oxidation of the aldose hemiacetals by iodine to generate the saccharide lactone intermediates, which underwent ammonolysis in situ to give the saccharide amides.
引用
收藏
页码:129 / 133
页数:5
相关论文
共 24 条
[1]   ANOMALOUS REACTION OF D-GLUCONAMIDE WITH BENZOYL CHLORIDE IN ANHYDROUS PYRIDINE [J].
DEFERRARI, JO ;
DELEDERK.RM ;
MATSUHIRO, B ;
LITTER, MI .
CARBOHYDRATE RESEARCH, 1970, 14 (01) :103-+
[2]   Acetylated Amides of aldonic acids [J].
Deulofeu, V ;
de Labriola, ER .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1939, 61 :1110-1111
[3]   SYNTHESIS OF A GLUCOSE-DERIVED TETRAZOLE AS A NEW BETA-GLUCOSIDASE INHIBITOR - A NEW SYNTHESIS OF 1-DEOXYNOJIRIMYCIN [J].
ERMERT, P ;
VASELLA, A .
HELVETICA CHIMICA ACTA, 1991, 74 (08) :2043-2053
[4]   A CONVENIENT PROCEDURE FOR THE SYNTHESIS OF 2,3,4,6-TETRA-O-BENZYL-D-GLUCONOLACTAM AND D-NOJIRILACTAM [J].
HOOS, R ;
NAUGHTON, AB ;
VASELLA, A .
HELVETICA CHIMICA ACTA, 1993, 76 (04) :1802-1807
[5]   CONFIRMATION OF THE STRUCTURES OF THE PRODUCTS OBTAINED ON ACYLATION OF 2-AMINO-2-DEOXY-D-GLUCONIC ACID [J].
HORTON, D ;
THOMSON, JK .
CARBOHYDRATE RESEARCH, 1989, 193 :49-60
[6]   The rotatory powers of the amides of several alpha-hydroxy acids of the sugar group [J].
Hudson, CS ;
Komatsu, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1919, 41 :1141-1147
[7]   The preparation of acetylaldonic acids [J].
Hurd, CD ;
Sowden, JC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1938, 60 :235-237
[8]  
KATRITZKY AR, 1989, SYNTHESIS-STUTTGART, P949
[9]  
KUHN R, 1959, LIEBIGS ANN CHEM, V628, P186
[10]   SYNTHESES WITH PARTIALLY BENZYLATED SUGARS .9. SYNTHESIS OF A 5-HEXULOSONIC ACID (5-KETOHEXONIC ACID) DERIVATIVE AND INVERSION OF CONFIGURATION AT C-5 IN AN ALDOSE [J].
KUZUHARA, H ;
FLETCHER, HG .
JOURNAL OF ORGANIC CHEMISTRY, 1967, 32 (08) :2535-&