Highly selective synthesis of 1-N-iminosugars of the D-glucose and -glucuronic acid types

被引:33
作者
Kim, YJ [1 ]
Ichikawa, M [1 ]
Ichikawa, Y [1 ]
机构
[1] Johns Hopkins Univ, Sch Med, Dept Pharmacol & Mol Sci, Baltimore, MD 21205 USA
关键词
D O I
10.1021/jo9917700
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
引用
收藏
页码:2599 / 2602
页数:4
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共 17 条
[1]   1-aza sugars, apparent transition state analogues of equatorial glycoside formation/cleavage [J].
Bols, M .
ACCOUNTS OF CHEMICAL RESEARCH, 1998, 31 (01) :1-8
[2]   TI(O-I-PR)4-MEDIATED NUCLEOPHILIC OPENINGS OF 2,3-EPOXY ALCOHOLS - A MILD PROCEDURE FOR REGIOSELECTIVE RING-OPENING [J].
CARON, M ;
SHARPLESS, KB .
JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (09) :1557-1560
[3]   (R)-2,3-O-CYCLOHEXYLIDENEGLYCERALDEHYDE, A VERSATILE INTERMEDIATE FOR ASYMMETRIC-SYNTHESIS OF CHIRAL ALCOHOL [J].
CHATTOPADHYAY, A ;
MAMDAPUR, VR .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (03) :585-587
[4]   FACILE CONVERSION OF EPOXIDES TO BETA-HYDROXY NITRILES UNDER ANHYDROUS CONDITIONS WITH LITHIUM CYANIDE [J].
CIACCIO, JA ;
STANESCU, C ;
BONTEMPS, J .
TETRAHEDRON LETTERS, 1992, 33 (11) :1431-1434
[5]   SELECTIVE OXIDATION OF ALDEHYDES TO CARBOXYLIC-ACIDS WITH SODIUM-CHLORITE HYDROGEN-PEROXIDE [J].
DALCANALE, E ;
MONTANARI, F .
JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (04) :567-569
[6]   PREPARATION AND SYNTHETIC UTILITY OF TERT-BUTYLDIPHENYLSILYL ETHERS [J].
HANESSIAN, S ;
LAVALLEE, P .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1975, 53 (19) :2975-2977
[7]   FACILE SYNTHESIS OF A NEW-TYPE OF IMINOSUGAR - A NITROGEN ATOM IS IN THE ANOMERIC POSITION [J].
ICHIKAWA, M ;
ICHIKAWA, Y .
BIOORGANIC & MEDICINAL CHEMISTRY, 1995, 3 (02) :161-165
[8]   1-N-iminosugars:: Potent and selective inhibitors of β-glycosidases [J].
Ichikawa, Y ;
Igarashi, Y ;
Ichikawa, M ;
Suhara, Y .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (13) :3007-3018
[9]   TOTAL SYNTHESIS OF (+)-NOJIRIMYCIN AND (+)-1-DEOXYNOJIRIMYCIN [J].
IIDA, H ;
YAMAZAKI, N ;
KIBAYASHI, C .
JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (15) :3337-3342
[10]   ISOFAGOMINE, A POTENT, NEW GLYCOSIDASE INHIBITOR [J].
JESPERSEN, TM ;
DONG, WL ;
SIERKS, MR ;
SKRYDSTRUP, T ;
LUNDT, I ;
BOLS, M .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1994, 33 (17) :1778-1779