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A new method for the synthesis of ureido sugars

✍ Scribed by Bogusława Piekarska-Bartoszewicz; Andrzej Temeriusz

Publisher
Elsevier Science
Year
1990
Tongue
English
Weight
388 KB
Volume
203
Category
Article
ISSN
0008-6215

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✦ Synopsis

Nitrosoureas are an important class of antitumor agents'. Analogues of streptozotocin (N-nitroso-N-methyl urea of 2-amino-2-deoxy-D-glucose)2*3 have been described and many other nitrosoureido sugars have been prepared4. Nitrosoureido sugars can be obtained easily by aqueous nitrosation of ureido sugars with sodium nitrite3. The most convenient method for the synthesis of ureido sugars involves the reaction of isocyanates with amino sugars', but few isocyanates are available commercially.

Recently, Izdebski and Pawlak'j described a convenient new method for the synthesis of NJV'-disubstituted ureas and we have adopted this method for the synthesis of ureido sugars.

Bis(4-nitrophenyl) carbonate (l), obtained6 by the action of phosgene on sodium 4_nitrophenolate, was reacted in dichloromethane in the presence of l-hydroxybenzotriazole with methyl 3,4,6-tri-O-acetyl-2-amino-2-deoxy-P-~-glucopyranoside to

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