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

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