SYNTHESIS OF TETRAZOLES BEARING A SUGAR MOIETY (SUGAR TETRAZOLES) - X-RAY MOLECULAR-STRUCTURE OF -BENZYLOXYMETHYL-6-OXA-1,5-PENTAMETHYLENETETRAZOLE

Thermolysis of perbenzylated D-glucopyranosediyl diazide 1 and D-galac topyranosediyl diazide 4 afforded, respectively, the corresponding 6-o xa-1,5-pentamethylenetetrazoles 2 and 5 via the sugar azido nitrenes, while, photolysis of diazides 1 and 4 gave, respectively, compounds 2 and 5 together with the corresponding byproducts, 10-oxa-1,5-pentameth ylenetetrazoles 3 and 6, Similarly, 5-(sugar chain)-substituted tetraz ole 9 was obtained by the thermolysis of perbenzylated 1,1-diazido acy clic sugar 8, while compound 9 and 1-(sugar chain)-substituted tetrazo le 10 were formed by the photolysis of compound 8. Interestingly, the thermolysis and photolysis of 1,1 -diazido-2,3-di-O-benzyl-D,L-glycera ldehyde 8f gave both the corresponding 9f and 10f.