Synthesis and reactions of 3,4-di-O-acetyl-6-amino-6-deoxy- and 6-acetamido-3,4-di-O-acetyl-6-deoxy-D-glucal.

The redn. of azidodeoxyglucal I (R = N3) with nickel boride gives the aminoglycal I (R = NH2); whereas redn. with thiolacetic acid leads directly to the amidoglycal I (R = NHAc). The aminoglycal I (R = NH2) is sensitive to aq. acid and rearranges to (1R)-(2-furyl)-2-acetamidoethanol. This furan give...

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Journal Title: Journal of Carbohydrate Chemistry Vol. 14; no. 3; pp. 287 - 297
Authors: Walter W. Zajac, William B. Mathews
Format: Article
Published: 1995
Application Date: Department Chemistry,Villanova University,Villanova,PA,USA.
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Summary: The redn. of azidodeoxyglucal I (R = N3) with nickel boride gives the aminoglycal I (R = NH2); whereas redn. with thiolacetic acid leads directly to the amidoglycal I (R = NHAc). The aminoglycal I (R = NH2) is sensitive to aq. acid and rearranges to (1R)-(2-furyl)-2-acetamidoethanol. This furan gives a Diels-Alder adduct II with N-phenylmaleimide in which the nitrogen and oxygen on the side chain have interchanged positions. In contrast, the amidoglycal I (R = NHAc) reacts with ammonium nitrate in trifluoroacetic anhydride and with acidic mercuric sulfate to give (E)-5-acetamido-(3S)-acetoxy-(4R)-formoxy-1-nitro-1-pentene and 6-acetamido-4-O-acetyl-2,3,6-trideoxy-aldehydo-D-erythro-trans-hex-2-enose resp. The amidoglycal I (R = NHAc) also undergoes an intramol. palladium (II) catalyzed intramol. cyclocondensation reaction leading to a pair of diastereomeric (4R)-acetoxy-7-acetyl-7-aza-2-oxabicyclo[3.2.1]oct-5-enes.
ISSN: 0732-8303