Zur Kondensation von Carbonylverbindungen mit Hydrazinen, XII: Über die Reaktionsprodukte des Hydrazins mit Zuckern

Stroh, Hans‐Hartwig; Arnold, Adolf; Scharnow, Hans‐G.

doi:10.1002/cber.19650980508

Cited by 11 publications

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“…The formation of cyclic hydrazide 5 was unexpected, but not unprecedented. [11] It did not impede the synthesis, however, because 5 could be hydrogenated with platinum catalyst to the acyclic hydrazine 6 in 80 % yield. The structure of 6 was also confirmed by X-ray crystallographic structure analysis (Figure 2).…”

Section: Resultsmentioning

confidence: 99%

Enantiospecific Synthesis of 1-Azafagomine

et al. 2000

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For the first time the two enantiomeric forms of the glycosidase inhibitor 1-azafagomine have been synthesised starting from D- and L-xylose. D-Xylose was converted to the 2,3,5-tribenzylfuranose, which upon reductive amination with tert-butyl carbazate gave the protected 1-hydrazino-1-deoxypentitol in high yield. N-acetylation, mesylation of the 4-OH, removal of the Boc group, cyclisation and deprotection gave (+)-1-azafagomine ((+)-1). By a similar sequence of reactions, L-xylose was converted to (-)-1-azafagomine ((-)-1). Enzymatic and other routes to optically pure 1-azafagomine were also studied. Compound (-)-1 is a potent competitive glycosidase inhibitor, while (+)-1 has no biological activity. The inhibition of almond beta-glucosidase by (-)-1 was found to be slow owing to a slow binding step of inhibitor to enzyme, with no subsequent conformational rearrangement. The rate constants for binding and release were found to be 3.3 x 10(4)M(-1)s(-1) and 0.011 s(-1), respectively, yielding Ki = 0.33 microM.

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Section: Resultsmentioning

confidence: 99%

Enantiospecific Synthesis of 1-Azafagomine

et al. 2000

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“…Formation of the ring was unexpected, but not unprecedented for carbohydrate hydrazones. 13 Nevertheless hydrogenation of 2 followed by acetylation of the nitrogen atom with Ac 2 O in MeOH gave acetate 3 in 80% yield.…”

Section: Methodsmentioning

confidence: 99%

Synthesis of (+)-Azafagomine from D-xylose

Ernholt

Thomsen

Jensen

et al. 1999

Synlett

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Zur Kondensation von Carbonylverbindungen mit Hydrazinen, XIII: Über die Reaktion von Alkyl‐ und Aralkylhydrazinen mit Zuckern

Stroh

Scharnow

1965

Chem. Ber.

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Alkyl‐ und Aralkylhydrazine kondensieren in Methanol oder 50‐proz. Äthanol analog den Arylhydrazinen bevorzugt mit Mannose, Galaktose, Rhamnose und Arabinose zu gut kristallisierenden Hydrazonen. Die Bildung von Hydrazonen der Glucose, Ribose und Lyxose läßt sich chromatographisch nachweisen, während Fructose und Sorbose keine Kondensation eingehen. An einigen Beispielen wird gezeigt, daß die Zucker‐alkylhydrazone vorwiegend in der acyclischen Form vorliegen.

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Zur Kondensation von Carbonylverbindungen mit Hydrazinen, XII: Über die Reaktionsprodukte des Hydrazins mit Zuckern

Abstract: Zucker kondensieren in Methanol mit der halbmolaren Menge HydrazinhydratLU Azinen. mit uberschussigem Hydrazinhydrat zu Hydrazonen, deren Bildung durch Hydrazinolyse der Azine erfolgt. Die so erhiiltlichen k i n e und deren Acetate liegen vorwiegend in der acyclischen Form vor.

Cited by 11 publications

References 11 publications

Enantiospecific Synthesis of 1-Azafagomine

Enantiospecific Synthesis of 1-Azafagomine

Synthesis of (+)-Azafagomine from D-xylose

Zur Kondensation von Carbonylverbindungen mit Hydrazinen, XIII: Über die Reaktion von Alkyl‐ und Aralkylhydrazinen mit Zuckern

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