A HIGHLY STEREOCONTROLLED SYNTHETIC APPROACH TO 1,6-DIDEOXY-6,6-DIFLUOROAZASUGAR DERIVATIVES

被引：23

作者：

KITAZUME, T

MURATA, K

OKABE, A

TAKAHASHI, Y

YAMAZAKI, T

机构：

[1] Department of Bioengineering, Tokyo Institute of Technology Nagatsuta, Midori-ku, Yokohama

来源：

TETRAHEDRON-ASYMMETRY | 1994年 / 5卷 / 06期

关键词：

D O I：

10.1016/0957-4166(94)80053-7

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The synthetic utility of (alpha R, 6R)- or (alpha R, 6S)-N-(methylbenzyl)-6-difluoromethyl-5,6-dihydro-4-pyridone 2, which was produced from the reaction of 1-methoxy-3-[(trimethylsilyl)oxy]-1,3-butadiene and (alpha R)- or (alpha S)-N-(2,2-difluoroethylidene)methylbenzylamine 1, is described. These materials are found to be potential intermediates for a highly stereocontrolled synthesis of 1,6-dideoxy-6,6-difluoroazasugar analogues.

引用

页码：1029 / 1040

页数：12

共 30 条

[1] A NEW APPROACH TO THE SYNTHESIS OF HEXOSES - AN ENTRY TO (+/-)-FUCOSE AND (+)-DAUNOSAMINE
DANISHEFSKY, SJ
MARING, CJ
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (05) : 1269 - 1274
[2] CHEMISTRY OF OXAZIRIDINES .1. SYNTHESIS AND STRUCTURE OF 2-ARENESULFONYL-3-ARYLOXAZIRIDINES - NEW CLASS OF OXAZIRIDINES
DAVIS, FA
LAMENDOLA, J
NADIR, U
KLUGER, EW
SEDERGRAN, TC
PANUNTO, TW
BILLMERS, R
JENKINS, R
TURCHI, IJ
WATSON, WH
CHEN, JS
KIMURA, M
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (06) : 2000 - 2005
[3] FACTORS INFLUENCING THE STEREOSELECTIVITY IN THE CYCLOADDITION OF IMINO-DIENOPHILES DERIVED FROM AMINO ETHERS, AMINO-ALCOHOLS, AND AMINO-ACID ESTERS
DEVINE, PN
REILLY, M
OH, T
[J]. TETRAHEDRON LETTERS, 1993, 34 (37) : 5827 - 5830
[4] THE EFFECT OF DEOXYMANNOJIRIMYCIN ON THE PROCESSING OF THE INFLUENZA VIRAL GLYCOPROTEINS
ELBEIN, AD
LEGLER, G
TLUSTY, A
MCDOWELL, W
SCHWARZ, R
[J]. ARCHIVES OF BIOCHEMISTRY AND BIOPHYSICS, 1984, 235 (02) : 579 - 588
[5] ASYMMETRIC OXYGENATION OF CHIRAL IMIDE ENOLATES - A GENERAL-APPROACH TO THE SYNTHESIS OF ENANTIOMERICALLY PURE ALPHA-HYDROXY CARBOXYLIC-ACID SYNTHONS
EVANS, DA
MORRISSEY, MM
DOROW, RL
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (14) : 4346 - 4348
[6] GLYCOSIDASE INHIBITION BY PLANT ALKALOIDS WHICH ARE STRUCTURAL ANALOGS OF MONOSACCHARIDES
EVANS, SV
FELLOWS, LE
SHING, TKM
FLEET, GWJ
[J]. PHYTOCHEMISTRY, 1985, 24 (09) : 1953 - 1955
[7] FELLOWS LE, 1987, CHEM BRIT, V23, P842
[8] NOVEL MANNOSIDASE INHIBITOR BLOCKING CONVERSION OF HIGH MANNOSE TO COMPLEX OLIGOSACCHARIDES
FUHRMANN, U
BAUSE, E
LEGLER, G
PLOEGH, H
[J]. NATURE, 1984, 307 (5953) : 755 - 758
[9] 1ST SYNTHESIS OF (1R,2R,3S,9S,9AR)-1,2,3,9-TETRAHYDROXY-QUINOLIZIDINE, A NOVEL ISOSTERIC HOMOLOG OF THE GLUCOSIDASE INHIBITOR CASTANOSPERMINE
GRADNIG, G
BERGER, A
GRASSBERGER, V
STUTZ, AE
LEGLER, G
[J]. TETRAHEDRON LETTERS, 1991, 32 (37) : 4889 - 4892
[10] INTERFERENCE WITH HIV-INDUCED SYNCYTIUM FORMATION AND VIRAL INFECTIVITY BY INHIBITORS OF TRIMMING GLUCOSIDASE
GRUTERS, RA
NEEFJES, JJ
TERSMETTE, M
DEGOEDE, REY
TULP, A
HUISMAN, HG
MIEDEMA, F
PLOEGH, HL
[J]. NATURE, 1987, 330 (6143) : 74 - 77

← 1 2 3 →