170898-77-8Relevant academic research and scientific papers
Novel degradation of sugar skeleton by diazidation
Yokoyama, Masataka,Kobayashi, Naoki,Hachiya, Takeshi,Kubo, Misao,Togo, Hideo
, p. 2989 - 2992 (1996)
O-Benzylated acyclic sugars are allowed to react with azidotrimethylsilane in the presence of boron trifluoride-diethyl ether to afford the corresponding 1,1-diazido sugars, cyano sugars, and interestingly, 1,1-diazido sugars degradated at the 1-position
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.
