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Crystal and molecular structure of α-d-ribopyranosylamine 1,3-(cyclic carbamate)

✍ Scribed by Peter Köll; József Kovács; Dirk Abeln; Jürgen Kopf

Publisher
Elsevier Science
Year
1993
Tongue
English
Weight
210 KB
Volume
239
Category
Article
ISSN
0008-6215

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✦ Synopsis

Cyclic carbamates of glycosylamines are accessible by the reaction of aldoses with potassium cyanate in aqueous solutions and of glycosyl azides with triphenylphosphine and carbon dioxide2^3 . Application of the latter method to O-D-gluco-and -D-xylo-pyranosyl azide gave the corresponding 1,2-(cyclic carbamates) in high yields . The analogous reaction of the corresponding a-glycosyl azides gave complex mixtures of products3 . The 1H and 13C NMR data indicated that a main by-product in each of the reactions of the a-D-gluco and a-D xylo azides was a 1,3-(cyclic carbamate) with the allo or ribo configuration, respec-tively3 . As there was no precedent for this unexpected inversion of configuration at C-3, the title compound 1 (19 in the preceding paper3) was subjected to X-ray analysis at 25°C in order to verify the structure .

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