Chemical Transformation of Uronic Acids leading to Aminocyclitols. II. Synthesis of Hexaacetyl-streptamine from N-Acetyl-D-glucosamine

Chemical Transformation of Uronic Acids leading to Aminocyclitols. II. Synthesis of Hexaacetyl-streptamine from N-Acetyl-D-glucosamine

By employing the oxidative decarboxylation reaction using lead tetraacetate and successive nitromethane cyclization reaction in the reaction sequence, N-acetyl-D-glucosamine (11a) has been converted to hexaacetyl-streptamine (20a) in 8% overall yield. It has been also suggested that the present tran...

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Veröffentlicht in:Chemical & pharmaceutical bulletin 1978/12/25, Vol.26(12), pp.3825-3831
Hauptverfasser: KITAGAWA, ISAO, KADOTA, AKIKO, YOSHIKAWA, MASAYUKI
Format: Artikel
Sprache:eng
Schlagworte:
hexaacetyl-streptamine
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Zusammenfassung:By employing the oxidative decarboxylation reaction using lead tetraacetate and successive nitromethane cyclization reaction in the reaction sequence, N-acetyl-D-glucosamine (11a) has been converted to hexaacetyl-streptamine (20a) in 8% overall yield. It has been also suggested that the present transformation would provide a versatile method for preparation of aminocyclitols from various types of uronic acids.
ISSN:0009-2363
1347-5223
DOI:10.1248/cpb.26.3825