Concepedia

Aminocyclitols. XVI. A Synthesis and Configurational Study of Dibromo-dideoxyinosamine

Tetsuo Suami, Seiichiro Ogawa, Yasuo Nakashima, Hiroshi Sano

Bulletin of the Chemical Society of Japan · 1967 · 11 citations · 8 references

DOI

Concepts

Abstract

Abstract Bromination of epi-inosamine-2 in a mixture of acetyl bromide and acetic anhydride afforded 1, 5-dibromo-1, 5-dideoxy-rac-inosamine-6. From this compound, two hitherto unknown inosadiamines: myo-inosadiamine-2, 4 and muco-inosadiamine-2, 3, were obtained by displacement of the bromo groups by azide ions, followed by hydrogenation. The configurations of the new compounds obtained were established by the nuclear magnetic resonance spectra.

References

8

Stereochemistry of Cyclic Amino-alcohols. Inversion, Retention and Participation

G. E. McCasland, Rachel Clark, Herbert E. Carter · Journal of the American Chemical Society · 1949 · 50 citations

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Debromination of Inositol Bromohydrins.<sup>*</sup> Synthesis of “Conduritol-B,” scylloQuercitol, and D,L-viboQuercitol<sup>1,2</sup>

G. E. McCasland, E. C. Horswill · Journal of the American Chemical Society · 1953 · 47 citations

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Cyclizations of Dialdehydes with Nitromethane. VII.<sup>1</sup> Preparation of neo-Inosadiamine-1,4<sup>2</sup>

Frieder W. Lichtenthaler, Hermann O. L. Fischer · Journal of the American Chemical Society · 1961 · 45 citations

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The Role of Neighboring Groups in Replacement Reactions. II. The Effects of Small Amounts of Water on the Reaction of Silver Acetate in Acetic Acid with Some Butene and Cyclohexene Derivatives<sup>1</sup>

S. Winstein, Robert E. Buckles · Journal of the American Chemical Society · 1942 · 43 citations

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The Role of Neighboring Groups in Replacement Reactions. XXI. Front-side Participation of the Acetoxy Group. Catalytic Effect of Acetic Acid on the Reaction of Glycols with Hydrogen Chloride<sup>1,2</sup>

Robert Boschan, S. Winstein · Journal of the American Chemical Society · 1956 · 32 citations

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