A general strategy towards the synthesis of 1-N-iminosugar type glycosidase inhibitors:: demonstration by the synthesis of D- as well as L-glucose type iminosugars (isofagomines)

被引:45
作者
Pandey, G [1 ]
Kapur, M [1 ]
机构
[1] Natl Chem Lab, Div Organ Chem Synth, Poona 411008, Maharashtra, India
关键词
D O I
10.1016/S0040-4039(00)01553-7
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Both enantiomers of isofagomine, the potent glycosidase inhibitor of a type 1-N-iminosugar have been synthesized by the intramolecular cyclization of the PET generated alpha -trimethylsilylmethylamine radical cation with the appropriate tethered acetylene moiety. (C) 2000 Published by Elsevier Science Ltd.
引用
收藏
页码:8821 / 8824
页数:4
相关论文
共 15 条
[11]   Synthesis of 2-substituted polyhydroxytetrahydropyrimidines (N-hydroxy cyclic guanidino-sugars):: Transition state mimics of enzymatic glycosidic cleavage [J].
Le, VD ;
Wong, CH .
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (08) :2399-2409
[12]   PHOTOINDUCED SET GENERATION OF ALPHA-AMINERADICALS - A PRACTICAL METHOD FOR THE SYNTHESIS OF PYRROLIDINES AND PIPERIDINES [J].
PANDEY, G ;
KUMARASWAMY, G ;
BHALERAO, UT .
TETRAHEDRON LETTERS, 1989, 30 (44) :6059-6062
[13]   PHOTOINDUCED ELECTRON-TRANSFER (PET) PROMOTED CYCLIZATIONS OF 1-[N-ALKYL-N-(TRIMETHYLSILYL)METHYL]AMINES TETHERED TO PROXIMATE OLEFIN - MECHANISTIC AND SYNTHETIC PERSPECTIVES [J].
PANDEY, G ;
REDDY, GD ;
KUMARASWAMY, G .
TETRAHEDRON, 1994, 50 (27) :8185-8194
[14]   INHIBITION OF HIV AND SIV INFECTIVITY BY BLOCKADE OF ALPHA-GLUCOSIDASE ACTIVITY [J].
RATNER, L ;
VANDERHEYDEN, N ;
DEDERA, D .
VIROLOGY, 1991, 181 (01) :180-192
[15]   ELECTROCHEMICAL OXIDATION OF ORGANOSILICON COMPOUNDS .7. THE ORIGIN OF BETA-SILICON EFFECT IN ELECTRON-TRANSFER REACTIONS OF SILICON-SUBSTITUTED HETEROATOM COMPOUNDS - ELECTROCHEMICAL AND THEORETICAL-STUDIES [J].
YOSHIDA, J ;
MAEKAWA, T ;
MURATA, T ;
MATSUNAGA, SI ;
ISOE, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (05) :1962-1970