TOTAL SYNTHESIS OF SIASTATIN-B AND ITS ENANTIOMER USING CARBOHYDRATE AS A CHIRAL EDUCT

被引:20
作者
NISHIMURA, Y
WANG, WM
KUDO, T
机构
[1] Institute of Microbial Chemistry, Shinagawa-ku, Tokyo 141
关键词
D O I
10.1246/bcsj.65.978
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The enantioselective synthesis of siastatin B, an inhibitor of neuraminidase and its antipode from D-ribono-gamma-lactone has stereospecifically been achieved. The total synthesis elucidated the absolute configuration of siastatin B as (3S,4S,5R,6R)-6-acetamido-4,5-dihydroxy-3-piperidinecarboxylic acid.
引用
收藏
页码:978 / 986
页数:9
相关论文
共 66 条
[41]   SIASTATIN-B, A POTENT NEURAMINIDASE INHIBITOR - THE TOTAL SYNTHESIS AND ABSOLUTE-CONFIGURATION [J].
NISHIMURA, Y ;
WANG, W ;
KONDO, S ;
AOYAGI, T ;
UMEZAWA, H .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (21) :7249-7250
[42]   THE NEF REACTION [J].
NOLAND, WE .
CHEMICAL REVIEWS, 1955, 55 (01) :137-155
[43]   OXIDATION OF NITRONATES WITH PERSULFATE AND WITH SILVER IONS [J].
PAGANO, AH ;
SHECHTER, H .
JOURNAL OF ORGANIC CHEMISTRY, 1970, 35 (02) :295-&
[44]  
Paulsen H, 1968, Adv Carbohydr Chem Biochem, V23, P115
[45]  
PAULSON JC, 1985, RECEPTORS, V2, P131
[46]   ISOLATION AND PROPERTIES OF A SIALIDASE FROM TRYPANOSOMA-RANGELI [J].
REUTER, G ;
SCHAUER, R ;
PRIOLI, R ;
PEREIRA, MEA .
GLYCOCONJUGATE JOURNAL, 1987, 4 (04) :339-348
[47]  
REUTTER W, 1982, SIALIC ACIDS CHEM ME, P263
[48]  
Rosenberg A, 1976, BIOL ROLES SIALIC AC, P295
[49]   SYNTHESIS OF BRANCHED-CHAIN NITRO AND AMINO SUGARS BY NITROMETHANE ROUTE [J].
ROSENTHA.A ;
ONG, KS ;
BAKER, D .
CARBOHYDRATE RESEARCH, 1970, 13 (01) :113-&
[50]   BRANCHED-CHAIN NITRO SUGARS - METHYL 4,6-O-BENZYLIDENE-2,3-DIODEOXY-3-C-NITROMETHYL-ALPHA-D-RIBO-HEXOPYRANOSIDE [J].
ROSENTHAL, A ;
SCHOLLNHAMMER, G .
CANADIAN JOURNAL OF CHEMISTRY-BACK YEAR, 1972, 50 (11) :1780-+