Di- und Polyaminozucker, XXVII1) Synthesen von Derivaten der 4,6-Diamino-4,6-didesoxy-D-glucose, 4,6-Diamino-4,6-didesoxy-D-gulose, 3,4,6-Triamino-3,4,6-tridesoxy-D-allose und 3,4,6-Triamino-3,4,6-tridesoxy-D-galactose

Synthese und Reaktionen der epimeren 3,4-Epoxyzucker 7 und 23 werden beschrieben. 7 lies sich mit Natriumazid stereoselektiv zu 8 offnen. Aus 8 wurde uber das Triflat 11 das Triazid 14 hergestellt. 8 und 14 wurden zu den reduzierenden Zuckern 13 und 16 umgesetzt. Die Offnung von 23 mit Natriumazid ergab 24 und 26 im Verhaltnis 3:2. 26 wurde in 31 ubergefuhrt. Das Triazid 32 war durch Azidolyse der Triflate 25 und 29 erhaltlich. Die Tosylierung von 36 fuhrte zu einem Gemisch aus 37 und 38. Aus 22 entstand unter Einwirkung von Natriummethylat ein Gemisch der Epoxide 7 und 23. Di- and Polyamino Sugars, XXVII1) – Syntheses of Derivatives of 4,6-Diamino-4,6-dideoxy-D-glucose, 4,6-Diamino-4,6-dideoxy-D-gulose, 3,4,6-Triamino-3,4,6-trideoxy-D-allose, and 3,4,6-Triamino-3,4,6-trideoxy-D-galactose Syntheses and reactions of the epimeric epoxy-sugars 7 and 23 are described. Stereoselective opening of 7 with sodium azide yielded 8 which was transformed into the triazide 14via the triflate 11. The reducing sugars 13 and 16 were prepared from 8 and 14. With sodium azide 23 reacted to form a 3:2 mixture of 24 and 26. The latter was converted into 31. The triazide 32 was obtainable by azidolysis of the triflates 25 and 29. Tosylation of 36 afforded a mixture of 37 and 38. Reaction of 22 with sodium methanolate led to a mixture of the epoxides 7 and 23.

[1]  Yousif Ali,et al.  Synthesis of derivatives of 4,6-diamino-4,6-dideoxy-d-gulose , 1979 .

[2]  D. Weisleder,et al.  O-ethylidene-D-allopyranoses: 1,2-O-,1,2:4,6-, and 2,3:4,6-di-O-ethylidene derivatives , 1975 .

[3]  J. Yoshimura,et al.  Aminosugars. XXIII. L-Idofuranose Derivatives Containing a Heterocycle at C-5,6 Position , 1975 .

[4]  D. Horton,et al.  Application of paramagnetic shift-reagents in conformational analysis. Conformations of some isopropylidenated pyranose derivatives☆ , 1975 .

[5]  J. Heitmann,et al.  An X-ray crystallographic study of a carbohydrate orthoester: 3,4,6-tri-O-acetyl-1,2-O-(1-exo-ethoxyethylidene)-α-D-glucopyranose , 1973 .

[6]  D. Weisleder,et al.  Dioxolane configuration in diastereoisomeric 1,2-O- and 1,2:4,6-di-O-alkylidene-α-d-glucopyranose derivatives by n.m.r. spectroscopy , 1972 .

[7]  B. Coxon.  Model parameters for the analysis of skew conformations of carbohydrates by p.m.r. spectroscopy , 1970 .

[8]  L. Hall,et al.  Studies of Carbohydrate derivatives by nuclear magnetic double-resonance Part II. A determination of the signs of proton-proton coupling-constants of saturated and unsaturated carbohydrates , 1968 .

[9]  A. C. Richardson,et al.  Nucleophilic replacement reactions of sulphonates : Part I. The preparation of derivatives of 4,6-diamino-4,6-dideoxy-D-glucose and -D-galactose , 1968 .

[10]  L. Goodman,et al.  A mild method for the hydrolysis of acetal groups attached to sugars and nucleosides , 1968 .

[11]  R. Lemieux,et al.  1,2-Alkylidene and 1,2-ortholactone derivatives of 3,4,6-tri-O-acetyl-α-D-glucose , 1968 .

[12]  D. Horton,et al.  Synthesis of 1,6-anhydro-β-d-talopyranose from derivatives of d-galactose and d-mannose , 1967 .

[13]  J. Fawcett,et al.  The crystal and molecular structure of 1,2-O-amino-isopropylidene-α-d-glucopyranose hydroiodide , 1966 .

[14]  J. Kovář,et al.  Über aminozucker VIII. Darstellung von derivaten der 3,6-diamino-3,6-didesoxy-D-allose , 1966 .

[15]  B. Coxon,et al.  The conformations of cyclic compounds in solution—II , 1964 .

[16]  E. Fischer,et al.  Teilweise Acylierung der mehrwertigen Alkohole und Zucker. IV.1): Derivate der d-Glucose und d-Fructose , 1918 .