A short synthesis of azasugars via aldol reaction of chelated amino acid ester enolates

被引：49

作者：

Grandel, R ^{[1
]}

Kazmaier, U ^{[1
]}

机构：

[1] UNIV HEIDELBERG,INST ORGAN CHEM,D-69120 HEIDELBERG,GERMANY

来源：

TETRAHEDRON LETTERS | 1997年 / 38卷 / 46期

关键词：

D O I：

10.1016/S0040-4039(97)10176-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Aldol reactions of chelated amino acid ester enolates with chiral aldehydes gives rise to polyhydroxylated amino acids in a highly stereoselective fashion. These oxygenated amino acids can be converted into polyhydroxylated pipecolinic acids and azasugars by cyclization using the Mitsunobu reaction. A interesting epimerization was observed during the cyclization. (C) 1997 Elsevier Science Ltd.

引用

页码：8009 / 8012

页数：4

共 42 条

[1] STEREOCONTROLLED SYNTHESIS OF 1,5-DIDEOXY-1,5-IMINO-ALLITOL (1-DEOXY-ALLONOJIRIMYCIN) FROM SERINE [J].

ALTENBACH, HJ ;

HIMMELDIRK, K .

TETRAHEDRON-ASYMMETRY, 1995, 6 (05) :1077-1080

[2] A FACILE, PRACTICAL SYNTHESIS OF 2,6-DIDEOXY-2,6-IMINO-7-O-BETA-D-GLUCOPYRANOSYL-D-GLYCERO-L-GULO-HEPTITOL (MDL 25,637) [J].

ANZEVENO, PB ;

CREEMER, LJ ;

DANIEL, JK ;

KING, CHR ;

LIU, PS .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (11) :2539-2542

[3] N-ALKYLATED NITROGEN-IN-THE-RING SUGARS - CONFORMATIONAL BASIS OF INHIBITION OF GLYCOSIDASES AND HIV-1 REPLICATION [J].

ASANO, N ;

KIZU, H ;

OSEKI, K ;

TOMIOKA, E ;

MATSUI, K ;

OKAMOTO, M ;

BABA, M .

JOURNAL OF MEDICINAL CHEMISTRY, 1995, 38 (13) :2349-2356

[4] THE SYNTHESIS OF POLYHYDROXYLATED AMINO-ACIDS FROM GLUCURONOLACTONE - ENANTIOSPECIFIC SYNTHESES OF 2S,3R,4R,5S-TRIHYDROXYPIPECOLIC ACID, 2R,3R,4R,5S-TRIHYDROXYPIPECOLIC ACID AND 2R,3R,4R-DIHYDROXYPROLINE [J].

BASHYAL, BP ;

CHOW, HF ;

FELLOWS, LE ;

FLEET, GWJ .

TETRAHEDRON, 1987, 43 (02) :415-422

[5] EXPEDITIOUS SYNTHESIS OF AZASUGARS BY THE DOUBLE REDUCTIVE AMINATION OF DICARBONYL SUGARS [J].

BAXTER, EW ;

REITZ, AB .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (11) :3175-3185

[6] 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

[7] SECRETION OF HUMAN HEPATITIS-B VIRUS IS INHIBITED BY THE IMINO SUGAR N-BUTYLDEOXYNOJIRIMYCIN [J].

BLOCK, TM ;

LU, XY ;

PLATT, FM ;

FOSTER, GR ;

GERLICH, WH ;

BLUMBERG, BS ;

DWEK, RA .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1994, 91 (06) :2235-2239

[8]

DENNIS JW, 1990, CANCER RES, V50, P1867

[9] 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

[10] THE EFFECT OF DEOXYMANNOJIRIMYCIN ON THE PROCESSING OF THE INFLUENZA VIRAL GLYCOPROTEINS [J].

ELBEIN, AD ;

LEGLER, G ;

TLUSTY, A ;

MCDOWELL, W ;

SCHWARZ, R .

ARCHIVES OF BIOCHEMISTRY AND BIOPHYSICS, 1984, 235 (02) :579-588

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