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Synthesis of 2-amino-2-deoxy- and 3-amino-3-deoxy-α-d-mannopyranosyl α-d-mannopyranoside by sequential osmylations of a dienic disaccharide

✍ Scribed by Hans H. Baer; Lisa Siemsen

Publisher
Elsevier Science
Year
1986
Tongue
English
Weight
766 KB
Volume
146
Category
Article
ISSN
0008-6215

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✦ Synopsis

Partial oxyamination of 4,6-di-0-acetyl-2,3-dideoxy-cu-D-erythro-hex-2enopyranosyl 4,6-di-O-acetyl-2,3-dideoxy-a-D-erythro-hex-Zenopyranoside with chloramine-T and osmium tetraoxide gave 4,6-di-0-acetyl-2-deoxy-2-(p-toluenesulfonamide)-a-D-mannopyranosyl 4,6-di-0-acetyl-2,3-dideoxy-ry-D-erythro-hex-2enopyranoside and its 3-deoxy-3-(p-toluenesulfonamido) regioisomer, each in l&19% isolated yield. Osmium tetraoxide-catalyzed cis-hydroxylation of the remaining alkenic residue in these products led in high yields to the corresponding triols having the a-D-manno, a-D-manno configuration. These were N-desulfonylated (and simultaneously 0-deacetylated) by the action of sodium in liquid ammonia to furnish 2-amino-Zdeoxy-cY-D-mannopyranosyl a-D-mannopyranoside and 3-amino-3-deoxy-cY-D-mannopyranosyl a-D-mannopyranoside as new, trehalose-type amino sugars.

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