The application of nitrido manganese reagents to the synthesis of protected N-methyl D-fucosamine

被引:15
作者
Carreira, EM [1 ]
Hong, J [1 ]
Du Bois, J [1 ]
Tomooka, CS [1 ]
机构
[1] CALTECH, Div Chem & Chem Engn 16430, Pasadena, CA 91125 USA
关键词
D O I
10.1351/pac199870051097
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A synthesis of protected D-fucosamine and N-methyl fucosamine from D-galactose is described. The synthesis is carried out in ten steps and includes the amination reaction of D-fucal with an easily prepared MnN reagent.
引用
收藏
页码:1097 / 1103
页数:7
相关论文
共 88 条
[81]  
SERFONTEIN WJ, 1964, TETRAHEDRON LETT, P1069
[82]  
Sharon N., 1975, COMPLEX CARBOHYDRATE
[83]  
Sheldon R. A., 1981, METAL CATALYZED OXID
[84]   SYNTHESIS OF BENZYL 2-AZIDO-2-DEOXY-4-O-BETA-D-GLUCOPYRANOSYL-ALPHA-D-GLUCOPYRANOSIDE AND 1,6-ANHYDRO-2-AZIDO-2-DEOXY-4-O-BETA-D-GLUCOPYRANOSYL-BETA-D-GLUCOPYRANOSE [J].
SHING, TKM ;
PERLIN, AS .
CARBOHYDRATE RESEARCH, 1984, 130 (JUL) :65-72
[85]  
SHOJI JI, 1961, J ANTIBIOT, V14, P27
[86]   SYNTHESIS OF 2,6-DIDEOXY-2-(N-METHYLACETAMIDO)-D-GALACTOSE (N-ACETYL-N-METHYL-D-FUCOSAMINE) AND OF DERIVATIVES SUITABLE FOR 3-O-GLYCOSYLATION OR 4-O-GLYCOSYLATION .9. CHEMISTRY OF BACTERIAL-ENDOTOXINS [J].
SZABO, P ;
CHARON, D .
CARBOHYDRATE RESEARCH, 1994, 257 (01) :145-153
[87]   FIRST ENANTIOSELECTIVE TOTAL SYNTHESIS OF (+)-PANCRATISTATIN - AN UNUSUAL SET OF PROBLEMS [J].
TIAN, XR ;
HUDLICKY, T ;
KONIGSBERGER, K .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (12) :3643-3644
[88]   OXIDATION OF ORGANIC COMPOUNDS WITH CERIUM(IV) .14. FORMATION OF ALPHA-AZIDO-BETA-NITRATOALKANES FROM OLEFINS, SODIUM AZIDE, AND CERIC AMMONIUM NITRATE [J].
TRAHANOVSKY, WS ;
ROBBINS, MD .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1971, 93 (20) :5256-+