152301-86-5Relevant academic research and scientific papers
Photolysis of Sugar Anomeric Diazides: Sugar-derived Tetrazoles as Evidences for a major Nitrene Decomposition Pathway
Praly, Jean-Pierre,Stefano, Carmela Di,Descotes, Gerard,Faure, Rene
, p. 89 - 92 (1994)
The preponderance of regioisomeric sugar-derived tetrazoles (up to 75percent total yield) obtained upon photolysis of protected (benzyl, acetyl) glucopyranosylidene diazides, even in the presence of added acrylonitrile, proved that azidonitrene intermediates predominate over anomeric carbenes, in the reaction.Reversions are presented for its mechanism and one structure.
Synthesis of 6-Oxa-1,5-Pentamethylenetetrazoles (Sugar Tetrazoles)
Yokoyama, Masataka,Matsushita, Michio,Hirano, Sachiko,Togo, Hideo
, p. 5097 - 5100 (1993)
Some sugar tetrazoles have been synthesized by the photolysis or the thermolysis of D-glucopyranosylidene diazide or D-galactopyranosylidene diazide.The reaction mechanism is discussed.
Synthesis of tetrazoles bearing a sugar moiety (sugar tetrazoles). X-Ray molecular structure of '(7R,8R,9S,10R)-8,9,10-tribenzyloxy-7-benzyloxymethyl-6-oxa-1,5-pentamethylenetetrazole'
Yokoyama, Masataka,Hirano, Sachiko,Matsushita, Michio,Hachiya, Takeshi,Kobayashi, Naoki,et al.
, p. 1747 - 1754 (2007/10/02)
Thermolysis of perbenzylated D-glucopyranosediyl diazide 1 and D-galactopyranosediyl diazide 4 afforded, respectively, the corresponding 6-oxa-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-pentamethylenetetrazoles 3 and 6.Similarly, 5-(sugar chain)-substituted tetrazole 9 was obtained by the thermolysis of perbenzylated 1,1-diazido acyclic sugar 8, while compound 9 and 1-(sugar chain)-substituted tetrazole 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-glyceraldehyde 8f gave both the corresponding 9f and 10f.
