TOTALLY SYNTHETIC ANALOGS OF SIASTATIN-B .1. OPTICALLY-ACTIVE 2-ACETAMIDOPIPERIDINE DERIVATIVES

被引：20

作者：

KUDO, T ^{[1
]}

NISHIMURA, Y ^{[1
]}

KONDO, S ^{[1
]}

TAKEUCHI, T ^{[1
]}

机构：

[1] INST MICROBIAL CHEM,3-14-23 KAMIOSAKI,SHINAGAWA KU,TOKYO 141,JAPAN

来源：

JOURNAL OF ANTIBIOTICS | 1992年 / 45卷 / 06期

关键词：

D O I：

10.7164/antibiotics.45.954

中图分类号：

Q81 [生物工程学（生物技术）]; Q93 [微生物学];

学科分类号：

071005 ; 0836 ; 090102 ; 100705 ;

摘要：

Totally synthetic analogues of siastatin B, optically active 2-acetamido-3,4,5-trihydroxypiperidines having the nitromethyl, aminomethyl and carboxyl branched groups at C-5 have been obtained from D-ribono-1,4-lactone by a stereospecific convergent method. Some analogues showed inhibitory activity against some glycosidases.

引用

页码：954 / 962

页数：9

共 11 条

[1] OXIDATION OF ALPHA,BETA-UNSATURATED ALDEHYDES [J].

BAL, BS ;

CHILDERS, WE ;

PINNICK, HW .

TETRAHEDRON, 1981, 37 (11) :2091-2096

[2] NEW AMINO-PROTECTING GROUPS IN ORGANIC SYNTHESIS [J].

CARPINO, LA .

ACCOUNTS OF CHEMICAL RESEARCH, 1973, 6 (06) :191-198

[3] OMEGA-ALDEHYDE SUGARS PREPARED BY NINHYDRIN OXIDATION [J].

GIBSON, AR ;

MELTON, LD ;

SLESSOR, KN .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1974, 52 (23) :3905-3912

[4] CONFIGURATIONAL EFFECTS ON THE PROTON MAGNETIC RESONANCE SPECTRA OF 6-MEMBERED RING COMPOUNDS [J].

LEMIEUX, RU ;

KULLNIG, RK ;

BERNSTEIN, HJ ;

SCHNEIDER, WG .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1958, 80 (22) :6098-6105

[5] PREPARATION OF BRANCHED-CHAIN NITRO AND AMINO SUGARS BY APPLICATION OF NITROMETHANE METHOD TO KETOSES [J].

LOURENS, GJ .

CARBOHYDRATE RESEARCH, 1971, 17 (01) :35-&

[6] OXIDATION OF LONG-CHAIN AND RELATED ALCOHOLS TO CARBONYLS BY DIMETHYL-SULFOXIDE ACTIVATED BY OXALYL CHLORIDE [J].

MANCUSO, AJ ;

HUANG, SL ;

SWERN, D .

JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (12) :2480-2482

[7] THE USE OF DIETHYL AZODICARBOXYLATE AND TRIPHENYLPHOSPHINE IN SYNTHESIS AND TRANSFORMATION OF NATURAL-PRODUCTS [J].

MITSUNOBU, O .

SYNTHESIS-STUTTGART, 1981, (01) :1-28

[8] SIASTATIN-B, A POTENT NEURAMINIDASE INHIBITOR - THE TOTAL SYNTHESIS AND ABSOLUTE-CONFIGURATION [J].

NISHIMURA, Y ;

WANG, W ;

KONDO, S ;

AOYAGI, T ;

UMEZAWA, H .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (21) :7249-7250

[9] TOTAL SYNTHESIS OF SIASTATIN-B AND ITS ENANTIOMER USING CARBOHYDRATE AS A CHIRAL EDUCT [J].

NISHIMURA, Y ;

WANG, WM ;

KUDO, T .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1992, 65 (04) :978-986

[10]

Nishimura Y., 1992, STUDIES NATURAL PROD, V10, P495

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