Synthesis of a 2-deoxy-ribose type 1-N-iminosugar

被引:38
作者
Makino, K [1 ]
Ichikawa, Y [1 ]
机构
[1] Johns Hopkins Univ, Sch Med, Dept Pharmacol & Mol Sci, Baltimore, MD 21205 USA
基金
美国国家卫生研究院;
关键词
D O I
10.1016/S0040-4039(98)01781-X
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A 2-deoxy-ribose-type 1-N-iminosugar 5 was synthesized, in multi-gram scale, from fumaric acid monoethyl ester employing Sharpless asymmetric epoxidation followed by a Lewis acid-catalyzed (Yamamoto's aluminum reagent) cyanide epoxy ring-opening reactions. (C) 1998 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:8245 / 8248
页数:4
相关论文
共 32 条
[1]   Nitrogen-containing furanose and pyranose analogues from Hyacinthus orientalis [J].
Asano, N ;
Kato, A ;
Miyauchi, M ;
Kizu, H ;
Kameda, Y ;
Watson, AA ;
Nash, RJ ;
Fleet, GWJ .
JOURNAL OF NATURAL PRODUCTS, 1998, 61 (05) :625-628
[2]   Synthesis of a ribofuranosyl cation mimic [J].
Bols, M .
TETRAHEDRON LETTERS, 1996, 37 (12) :2097-2100
[3]   SYNTHESIS OF 2(R),5(R)-BIS(HYDROXYMETHYL)-3(R),4(R)-DIHYDROXYPYRROLIDINE - A NOVEL GLYCOSIDASE INHIBITOR [J].
CARD, PJ ;
HITZ, WD .
JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (06) :891-893
[4]   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
[5]   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
[6]   NUCLEAR MAGNETIC-RESONANCE ENANTIOMER REAGENTS - CONFIGURATIONAL CORRELATIONS VIA NUCLEAR MAGNETIC-RESONANCE CHEMICAL-SHIFTS OF DIASTEREOMERIC MANDELATE, O-METHYLMANDELATE, AND ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETATE (MTPA) ESTERS [J].
DALE, JA ;
MOSHER, HS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (02) :512-519
[7]   Chemistry of glycosylases and endonucleases involved in base-excision repair [J].
David, SS ;
Wiliams, SD .
CHEMICAL REVIEWS, 1998, 98 (03) :1221-1261
[8]   TETRAZOLES OF MANNO-FURANOSES AND RHAMNO-FURANOSES [J].
DAVIS, B ;
BRANDSTETTER, TW ;
SMITH, C ;
HACKETT, L ;
WINCHESTER, BG ;
FLEET, GWJ .
TETRAHEDRON LETTERS, 1995, 36 (41) :7507-7510
[9]   DESIGN SYNTHESIS AND PRELIMINARY EVALUATION OF A POTENT ALPHA-MANNOSIDASE INHIBITOR - 1,4-DIDEOXY-1,4-IMINO-D-MANNITOL [J].
FLEET, GWJ ;
SMITH, PW ;
EVANS, SV ;
FELLOWS, LE .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1984, (18) :1240-1241
[10]   SYNTHESIS OF PYRROLIDIN-1-YL ANALOGS OF PYRIMIDINE DIDEOXYNUCLEOSIDES [J].
HARNDEN, MR ;
JARVEST, RL .
TETRAHEDRON LETTERS, 1991, 32 (31) :3863-3866