Synthese der γ‐Octose des Chinocyclin‐Komplexes

Paulsen, Hans; Sinnwell, Volker

doi:10.1002/ange.19760881405

Cited by 7 publications

(1 citation statement)

References 4 publications

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“…7 . C,,H,,N,O,requires C,68.3;H,5.5;N,3,x-~-atlo-PjJYanoside (36) and -plopyvanoside (37) .-Compound (I)) (6.5 g ) in ethanol (50 nil) was treated with benzylaniine (4 nil) and tlie mixture was stirred a t 40 "C for 1.5 h . It was added t o a suspension of Raney nickel (15 g) in ethanol (50 ml) and shaken with hydrogen ( 4 atni) a t room temperature.…”

Section: 4y0)mentioning

confidence: 99%

Arylazo-glycenosides. Part 7. Syntheses of amino-sugars from methyl arylazo-hexenopyranosides

Hajivarnava¹,

Overend²,

Williams³

1982

J. Chem. Soc., Perkin Trans. 1

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Reaction of the anhydro-glycopyranosiduloses (1 ) and ( 2) with o-nitro-and o,p-dinitro-phenylhydrazine yielded the hydrazones (3)-( 6), whereas phenyl-or p-nitrophenyl-hydrazine yielded the phenylatoalkenes ( 7)-(lo), formed by rearrangement of intermediate hydrazones. Reaction of the azoalkanes ( 8) and ( 9) with a range of nuceophiles yielded the &-substituted phenylhydrazones (1 1 )-( 19) and ( 24)-( 28), respectively, by 1,4addition. It has been shown that the a-amino-hydrazones ( 20), ( 25), and ( 28) can be reduced to vicinal diaminosugars, thereby providing a new route to these compounds. Reduction of the azoalkene (9) yielded the 2-amino-2,3,6-trideoxy-hexopyranoside, isolated as the ON-diacetyl derivative (31 ). N SCHEME I ( O W s, 10.35 3.52 s, 10.12Ji,z J2.3

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Section: 4y0)mentioning

confidence: 99%