Glycosides of 2-acetamido-2-deoxy-D-glucosamine and benzylidene derivatives

被引:62
作者
Roth, Wolfgang [1 ]
Pigman, Ward
机构
[1] Univ Alabama, Med Ctr, Dept Med, Arthritis Res Lab, Birmingham, AL 35294 USA
[2] Univ Alabama, Med Ctr, Dept Biochem, Arthritis Res Lab, Birmingham, AL 35294 USA
关键词
D O I
10.1021/ja01502a041
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The methylation of 2-acetamido-2-deoxy-4,6-O-benzylidene-D-glucopyranose is a convenient method for the preparation of pure methyl alpha- and beta-glycosides of D-glucosamine. The anomeric configuration of the glycosides depends on the solvent. New physical constants are given for 2-acetamido-2-deoxy-4,6-O-benzylidene-D-glueopyranose, methyl. 2-acetamido-2-deoxy-4,6-O-benzylidene-beta-D-glucopyranoside, methyl 2-acetamido-2-deoxy-3-O-methyl-4,6-O-benzylidene-beta-D-glucopyranoside, methyl 2-acetamido-2-deoxy-4,6-0-benzylidene-a-D-glucopyranoside. The following new compounds are described: methyl 2-acetamido-2-deoxy-5,6-O-benzylidene-beta-D-glucofuranoside, methyl 2-acetamido-2-deoxy-3-O-methyl-5,6-O-benzylidene-beta-D-glucofuranoside and methyl 2-acetamido-2-deoxy-3-O-methyl-beta-D-glucofuranoside.
引用
收藏
页码:4608 / 4611
页数:4
相关论文
共 8 条
[1]   Methylation of glucosamine [J].
Cutler, WO ;
Haworth, WN ;
Peat, S .
JOURNAL OF THE CHEMICAL SOCIETY, 1937, :1979-1983
[2]  
ISBELL HS, 1940, J RES NATL BUR STAND, V24, P126
[3]   REINDARSTELLUNG VON ALPHA-METHYL-N-ACETYL-D-GLUCOSAMINID [J].
KUHN, R ;
ZILLIKEN, F ;
GAUHE, A .
CHEMISCHE BERICHTE-RECUEIL, 1953, 86 (04) :466-467
[4]  
MASAMUNE H, 1958, TOHOKU J EXP MED, V68, P181
[5]   Preparation and configurative relationships of methylglucosaminides [J].
Neuberger, A ;
Rivers, RP .
JOURNAL OF THE CHEMICAL SOCIETY, 1939, :122-126
[6]   The preparation of 3-methyl glucosamine [J].
Neuberger, A .
JOURNAL OF THE CHEMICAL SOCIETY, 1941, :50-51
[7]   Representation of beta-methylglucosides. [J].
Schlubach, HH ;
Maurer, K .
BERICHTE DER DEUTSCHEN CHEMISCHEN GESELLSCHAFT, 1924, 57 :1686-1687
[8]  
WHITEHOUSE MW, 1958, TETRAHEDRON, V4, P425