SYNTHESIS OF DEOXYMANNOJIRIMYCIN FAGOMINE DEOXYNOJIRIMYCIN 2-ACETAMIDO-1,5-IMINO-1,2,5-TRIDEOXY-D-MANNITOL 2-ACETAMIDO-1,5-IMINO-1,2,5-TRIDEOXY-D-GLUCITOL 2S, 3R, 4R, 5R-TRIHYDROXYPIPECOLIC ACID AND 2S, 3R, 4R, 5S-TRIHYDROXYPIPECOLIC ACID FROM METHYL 3-O-BENZYL-2,6-DIDEOXY-2,6-IMINO-ALPHA-D-MANNOFURANOSIDE

被引:110
作者
FLEET, GWJ [1 ]
FELLOWS, LE [1 ]
SMITH, PW [1 ]
机构
[1] ROYAL BOT GARDENS,JODRELL LAB,RICHMOND TW9 9DS,SURREY,ENGLAND
关键词
D O I
10.1016/S0040-4020(01)90035-3
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:979 / 990
页数:12
相关论文
共 33 条
[1]   NEW AND SELECTIVE REACTIONS AND REAGENTS IN CARBOHYDRATE-CHEMISTRY [J].
BARTON, DHR ;
MOTHERWELL, WB .
PURE AND APPLIED CHEMISTRY, 1981, 53 (01) :15-31
[2]   ENANTIOSPECIFIC SYNTHESES OF 2S,3R,4R,5S-TRIHYDROXYPIPECOLIC ACID, 2R,3R,4R,5S-TRIHYDROXYPIPECOLIC ACID, 2S,4S,5S-DIHYDROXYPIPECOLIC ACID, AND BULGECININE FROM DEUTERIUM-GLUCURONOLACTONE [J].
BASHYAL, BP ;
CHOW, HF ;
FLEET, GWJ .
TETRAHEDRON LETTERS, 1986, 27 (27) :3205-3208
[3]  
BASHYAL BP, 1987, IN PRESS TETRAHEDRON
[4]   SYNTHESIS OF 2S-CARBOXY-3R,4R,5S-TRIHYDROXYPIPERIDINE - A NATURALLY-OCCURRING INHIBITOR OF BETA-D-GLUCURONIDASE [J].
BERNOTAS, RC ;
GANEM, B .
TETRAHEDRON LETTERS, 1985, 26 (41) :4981-4982
[5]   SPECIFIC-INHIBITION OF HUMAN BETA-D-GLUCURONIDASE AND ALPHA-L-IDURONIDASE BY A TRIHYDROXY PIPECOLIC ACID OF PLANT-ORIGIN [J].
DIBELLO, IC ;
DORLING, P ;
FELLOWS, L ;
WINCHESTER, B .
FEBS LETTERS, 1984, 176 (01) :61-64
[6]   LACK OF GLYCOSIDASE INHIBITION BY, AND ISOLATION FROM XANTHOCERCIS-ZAMBESIACA (LEGUMINOSAE) OF, 4-0-(BETA-D-GLUCOPYRANOSYL)-FAGOMINE [1,2,5-TRIDEOXY-4-0-(BETA-D-GLUCOPYRANOSYL)-1,5-IMINO-D-ARABINO-HEXITOL], A NOVEL GLUCOSIDE OF A POLYHYDROXYLATED PIPERIDINE ALKALOID [J].
EVANS, SV ;
HAYMAN, AR ;
FELLOWS, LE ;
SHING, TKM ;
DEROME, AE ;
FLEET, GWJ .
TETRAHEDRON LETTERS, 1985, 26 (11) :1465-1468
[7]   GLYCOSIDASE INHIBITION BY PLANT ALKALOIDS WHICH ARE STRUCTURAL ANALOGS OF MONOSACCHARIDES [J].
EVANS, SV ;
FELLOWS, LE ;
SHING, TKM ;
FLEET, GWJ .
PHYTOCHEMISTRY, 1985, 24 (09) :1953-1955
[8]   ISOLATION AND STRUCTURE OF AN UNUSUAL CYCLIC AMINO ALDITOL FROM A LEGUME [J].
FELLOWS, LE ;
BELL, EA ;
LYNN, DG ;
PILKIEWICZ, F ;
MIURA, I ;
NAKANISHI, K .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1979, (22) :977-978
[9]   THE BIOLOGICAL-ACTIVITY OF POLYHYDROXYALKALOIDS FROM PLANTS [J].
FELLOWS, LE .
PESTICIDE SCIENCE, 1986, 17 (05) :602-606
[10]   SYNTHESIS OF 2-ACETAMIDO-1,5-IMINO-1,2,5-TRIDEOXY-D-MANNITOL AND OF 2-ACETAMIDO-1,5-IMINO-1,2,5-TRIDEOXY-D-GLUCITOL, A POTENT AND SPECIFIC INHIBITOR OF A NUMBER OF BETA-N-ACETYLGLUCOSAMINIDASES [J].
FLEET, GWJ ;
SMITH, PW ;
NASH, RJ ;
FELLOWS, LE ;
PAREKH, RB ;
RADEMACHER, TW .
CHEMISTRY LETTERS, 1986, (07) :1051-1054