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Studies of the synthesis of 1,2-cis-(cyclic carbamates) of α-d-aldopyranosylamines

✍ Scribed by József Kovács; István Pintér; Gábor Tóth; Zoltán Györgydeák; Peter Köll

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

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✦ Synopsis

Reaction of cr-Dghmopyranosyl aside with triphenylphosphine and carbon dioxide gave l-N,2-Ocarbonykx-D-glucopyranosylamine (7) and its a-&manose analogue (11, and I-N,3-O-carbonyl-cr-D-allofuranosylamine (15) and its a-D-pyranose analogue (17). Similarly, cr-o-xylopyranosyl azide gave l-N,2-O-carbonyl-a-~xylopyranosylamine (9) and its cY-D-furanose analogue (31, and I-N,3-O-carbonylo-rxibopyranosylamine (19) and its #X-n-xylopyranose analogue (21). The structures of the products and their acetylated derivatives were established by 'H and 13C NMR spectroscopy. I-N,3-o-Carbonyl-p-Dxylopyranosylamine (21) was obtained from /3-o-xylopyranosyl aside when spontaneous rearrangement of the 1,2kyclic carbamate) 5 into 21 occurred in water.

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