TOTAL SYNTHESES OF ENANTIOMERICALLY PURE D-GLYCOSYL AND L-GLYCOSYL DONORS AS COMPONENTS OF SANNAMYCIN-TYPE AMINOGLYCOSIDE ANTIBIOTICS

被引：9

作者：

LUDIN, C ^{[1
]}

SCHWESINGER, B ^{[1
]}

SCHWESINGER, R ^{[1
]}

MEIER, W ^{[1
]}

SEITZ, B ^{[1
]}

WELLER, T ^{[1
]}

HOENKE, C ^{[1
]}

HAITZ, S ^{[1
]}

ERBECK, S ^{[1
]}

PRINZBACH, H ^{[1
]}

机构：

[1] UNIV FREIBURG, INST ORGAN CHEM & BIOCHEM, CHEM LAB, D-79104 FREIBURG, GERMANY

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1994年 / 19期

关键词：

D O I：

10.1039/p19940002685

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Both enantiomers of purpurosaminides C (ent-7b, 13a-c), of a 2-azido analogue (ent-16b) and of 2-azido epimers (ent-26b, ent-29b), suitably protected for their direct use as glycosyl donors, are prepared from racemic 3,4-dihydro-2H-pyran-2-carbaldehyde (acrolein dimer, rac-1). The latter has been resolved on a preparative scale through the diastereoisomeric trifluoroacetylated 1'-amines obtained with (1R)- and (1S)-1 phenylethylamine, which allowed the combination of optical resolution with the introduction of the glycosyl 6-amino function.

引用

页码：2685 / 2701

页数：17

共 99 条

[1] STUDIES OF THE STEREOSELECTIVE REDUCTION OF 2-HYDROXYIMINO-HEXOPYRANOSIDES - LIBH4-ME(3)SICL, A MILD REDUCING AGENT OF OXIMES TO AMINES [J].

BANASZEK, A ;

KARPIESIUK, W .

CARBOHYDRATE RESEARCH, 1994, 251 :233-242

[2] SYNTHESIS OF OLIGOSACCHARIDES OF 2-AMINO-2-DEOXY SUGARS [J].

BANOUB, J ;

BOULLANGER, P ;

LAFONT, D .

CHEMICAL REVIEWS, 1992, 92 (06) :1167-1195

[3]

BeMiller J N, 1967, Adv Carbohydr Chem Biochem, V22, P25, DOI 10.1016/S0096-5332(08)60151-4

[4]

BOULLANGER P, 1976, CARBOHYD RES, V55, P55

[5] SYNTHESES OF DERIVATIVES OF 2,6-DIAMINO-2,3,4,6-TETRADEOXY-D-ERYTHROHEXOSE (PURPUROSAMINE-C), A COMPONENT OF GENTAMYCIN-C1A [J].

BRIMACOMBE, JS ;

DAABOUL, I ;

TUCKER, LCN .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1975, (10) :979-984

[6] STUDIES RELATED TO THE SYNTHESIS OF DERIVATIVES OF 2,6-DIAMINO-2,3,4,6-TETRADEOXY-D-ERYTHRO-HEXOSE (PURPUROSAMINE-C), A COMPONENT OF GENTAMICIN-C-1A [J].

BRIMACOMBE, JS ;

HUNEDY, F ;

MATHER, AM ;

TUCKER, LCN .

CARBOHYDRATE RESEARCH, 1979, 68 (02) :231-238

[7] SYNTHESES OF DERIVATIVES OF 2,6-DIAMINO-2,3,4,6-TETRADEOXY-DL-ERYTHRO-HEXOSE (DL-PURPUROSAMINE C) AND 2,6-DIAMINO-2,3,4,6-TETRADEOXY-DL-THREO-HEXOSE (EPI-DL-PURPUROSAMINE C) [J].

BRIMACOMBE, JS ;

DAABOUL, I ;

TUCKER, LCN .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1974, (02) :263-267

[8] GLYCOSYLPHOSPHONATES OF 2-AMINO-2-DEOXY-ALDOSES - SYNTHESIS OF A PHOSPHONATE ANALOG OF LIPID X [J].

BRINER, K ;

VASELLA, A .

HELVETICA CHIMICA ACTA, 1987, 70 (05) :1341-1356

[9] MECHANISMS OF REACTIONS IN THE SUGAR SERIES .1. THE ACID-CATALYSED HYDROLYSIS OF ALPHA-METHYL AND BETA-METHYL AND ALPHA-PHENYL AND BETA-PHENYL D-GLUCOPYRANOSIDES [J].

BUNTON, CA ;

LEWIS, TA ;

LLEWELLYN, DR ;

VERNON, CA .

JOURNAL OF THE CHEMICAL SOCIETY, 1955, :4419-4423

[10] SYNTHESIS OF RACEMIC PURPUROSAMINE-B [J].

CHMIELEWSKI, M ;

KONOWAL, A ;

ZAMOJSKI, A .

CARBOHYDRATE RESEARCH, 1979, 70 (02) :275-282

← 1 2 3 4 5 6 7 8 9 10 →